JP2002338508A - Fluorinating agent and method for producing 1-alkoxy-2- fluoro-3-hydroxy compound by nucleophilic ring-opening fluorination to 1-alkoxy-2, 3-epoxy compound - Google Patents
Fluorinating agent and method for producing 1-alkoxy-2- fluoro-3-hydroxy compound by nucleophilic ring-opening fluorination to 1-alkoxy-2, 3-epoxy compoundInfo
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新規フッ素化剤お
よび１−アルコキシ−２，３−エポキシ化合物の求核的
開環フッ素化反応への利用に関する。The present invention relates to a novel fluorinating agent and the use of 1-alkoxy-2,3-epoxy compounds for nucleophilic ring-opening fluorination.
【０００２】[0002]
【従来の技術】エポキシ化合物の開環フッ素化におい
て、フッ素化剤の選択は重要な問題である。フッ素化剤
としてフッ化水素を単独で用いると、操作性が悪く危険
である上、重合が進行してしまう場合があり、目的物は
得られない。また、三フッ素ホウ素を用いた場合は、転
移反応が進行してしまい、位置および立体的制御が難し
い。BACKGROUND OF THE INVENTION In ring-opening fluorination of epoxy compounds, selection of a fluorinating agent is an important problem. When hydrogen fluoride is used alone as the fluorinating agent, the operability is poor and dangerous, and the polymerization may proceed in some cases, and the desired product cannot be obtained. When boron trifluoride is used, the transfer reaction proceeds, and it is difficult to control the position and stericity.
【０００３】特に、２，３−エポキシアルコール類の求
核的フッ素化開環は、位置および立体化学制御が難し
く、幾つかのフッ素化剤が試されているが、従来法のほ
とんどが、Ｃ−３位選択的なフッ素化であった。例えば
Tetrahedron Lett.,1990,31(49),7209-7212（フッ素化
剤：K2HF2／H2F3NBu4）、J.Org.Chem.,1988,53,1026-10
30（フッ素化剤：ジイソプロピルアミントリハイドロフ
ルオライド）Tetrahedoron Lett.,1992,33,(47),7083-7
086(フッ素化剤：(HF)2/NBu4F）、Tetrahedoron Lett.,
1992,33,(47),7087-7088(フッ素化剤：(RO)4-nTiFn）の
合成例が示されているが、いずれもＣ−３位にフッ素が
結合した化合物が主成分として生成する。唯一、J.Org.
Chem.,1988,53,1026-1030に記載されている合成例でフ
ッ素化剤としてピリジンポリハイドロフルオライドを用
いた場合においてＣ−２位とＣ−３位が同等の割合で生
成しているが、Ｃ−２選択的な生成物を与える合成例
は、これまで報告されていない。In particular, nucleophilic fluorinated ring-opening of 2,3-epoxy alcohols is difficult to control the position and stereochemistry, and several fluorinating agents have been tried. The fluorination was -3 position selective. For example
Tetrahedron Lett., 1990, 31 (49), 7209-7212 (fluorinating agent: K 2 HF 2 / H 2 F 3 NBu 4 ), J. Org. Chem., 1988, 53, 1026-10.
30 (fluorinating agent: diisopropylamine trihydrofluoride) Tetrahedoron Lett., 1992, 33, (47), 7083-7
086 (fluorinating agent: (HF) 2 / NBu 4 F), Tetrahedoron Lett.,
1992, 33, (47), 7087-7088 (fluorinating agent: (RO) 4-n TiF n ) are shown as examples of synthesis, but in each case, a compound in which fluorine is bonded to the C-3 position is the main component. Generate as Only, J.Org.
Chem., 1988, 53, 1026-1030, the C-2 and C-3 positions are formed in the same ratio when pyridine polyhydrofluoride is used as the fluorinating agent in the synthesis example. However, no synthetic example giving a C-2 selective product has been reported so far.
【０００４】[0004]
【発明が解決しようする課題】本発明は、１−アルコキ
シ−２，３−エポキシ化合物の開環フッ素化において、
Ｃ−２位選択的フッ素化を進行させるようなフッ素化剤
およびその利用法の提供を目的とする。DISCLOSURE OF THE INVENTION The present invention relates to a ring-opening fluorination of a 1-alkoxy-2,3-epoxy compound.
An object of the present invention is to provide a fluorinating agent that promotes C-2 selective fluorination and a method of using the same.
【０００５】[0005]
【問題を解決するための手段】本発明者は上記の課題を
解決すべく鋭意検討した結果、フッ化水素酸アンモニウ
ム塩と４族遷移金属フッ化物塩とからなるフッ素化剤
が、１−アルコキシ−２，３−エポキシ化合物に対し、
Ｃ−２位選択的に開環フッ素化することを見出し、本発
明に至った。The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a fluorinating agent comprising an ammonium hydrofluorate salt and a Group 4 transition metal fluoride salt is a 1-alkoxy compound. For a -2,3-epoxy compound,
The present inventors have found that ring-opening fluorination is selectively performed at the C-2 position, leading to the present invention.
【０００６】すなわち、本発明は、一般式［１］That is, the present invention provides a compound represented by the general formula [1]:
【０００７】[0007]
【化４】 Embedded image
【０００８】［式中、ＲはＣ1-10の直鎖あるいは分岐ア
ルキル基を表す］で示されるフッ化水素酸アンモニウム
塩と４族遷移金属フッ化物塩とからなるフッ素化剤であ
る。Wherein R represents a C 1-10 linear or branched alkyl group, and a fluorinating agent comprising an ammonium hydrofluoride salt and a Group 4 transition metal fluoride salt.
【０００９】また、本発明は、４族遷移金属フッ化物塩
がチタン、ジルコニウム、ハフニウムの金属フッ化物で
ある上記に記載のフッ素化剤である。Further, the present invention is the above-mentioned fluorinating agent, wherein the Group 4 transition metal fluoride salt is a metal fluoride of titanium, zirconium or hafnium.
【００１０】また、本発明は、 一般式［２］Further, the present invention provides a compound represented by the general formula [2]:
【００１１】[0011]
【化５】 Embedded image
【００１２】［式中、Ｒ1およびＲ2は水素、Ｃ1-10置換
または無置換の飽和または不飽和の直鎖または分岐アル
キル基、Ｃ3-8環状アルキル基、無置換もしくは置換ア
リール基、無置換もしくは置換ヘテロ環を表し、同一で
も異なっていてもよい］で示される１−アルコキシ−
２，３−エポキシ化合物に上記に記載のフッ素化剤を作
用させて開環フッ素化し、一般式［３］Wherein R 1 and R 2 are hydrogen, C 1-10 substituted or unsubstituted saturated or unsaturated linear or branched alkyl group, C 3-8 cyclic alkyl group, unsubstituted or substituted aryl group Represents an unsubstituted or substituted heterocyclic ring, and may be the same or different].
The 2,3-epoxy compound is reacted with the above-mentioned fluorinating agent to effect ring-opening fluorination to give a compound of the general formula [3]
【００１３】[0013]
【化６】 Embedded image
【００１４】［式中、Ｒ1およびＲ2は一般式［２］と同
じ］で示される１−アルコキシ−２−フルオロ−３−ヒ
ドロキシロ化合物を製造する方法である。This is a method for producing a 1-alkoxy-2-fluoro-3-hydroxylo compound represented by the formula: wherein R 1 and R 2 are the same as in the general formula [2].
【００１５】[0015]
【発明の実施の形態】本発明に用いるフッ素化剤は、フ
ッ化水素酸アンモニウム塩と４族遷移金属フッ化物塩を
室温で混合することにより調製できる。フッ化水素酸ア
ンモニウム塩は、一般式［１］に示すようなアンモニウ
ム４級塩で、テトラアルキルアンモニウム ジハイドロ
ジェントリフルオライド類（Ｈ2Ｆ3ＮＲ4）である。DESCRIPTION OF THE PREFERRED EMBODIMENTS The fluorinating agent used in the present invention can be prepared by mixing ammonium hydrofluoride and a Group 4 transition metal fluoride at room temperature. The ammonium hydrofluoride is an ammonium quaternary salt represented by the general formula [1], and is a tetraalkylammonium dihydrogentrifluoride (H 2 F 3 NR 4 ).
【００１６】ここで、ＲはＣ1-10の直鎖あるいは分岐の
アルキル基を示す。具体的には、直鎖アルキル基とし
て、メチル、エチル、プロピル、ブチル、ペンチル、ヘ
キシル、ヘプチル、オクチル、デシル等を、また分岐ア
ルキル基として、イソプロピル、ｓｅｃ−ブチル、ｔｅ
ｒｔ−ブチル、２−メチルブチル、イソペンチル、イソ
ヘキシル、３−エチルオクチル、等を示すことができ
る。Here, R represents a C 1-10 linear or branched alkyl group. Specifically, as a linear alkyl group, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl and the like, and as a branched alkyl group, isopropyl, sec-butyl, te
Examples thereof include rt-butyl, 2-methylbutyl, isopentyl, isohexyl, and 3-ethyloctyl.
【００１７】また、４属遷移金属フッ化物塩は、チタ
ン、ジルコニウム、ハフニウムの金属フッ化物であり、
具体的には、四フッ化チタン、三フッ化チタン、四フッ
化ジルコニウム、四フッ化ハフニウムを挙げることがで
き、特に四フッ化ジルコニウム、四フッ化ハフニウムが
好ましい。The Group 4 transition metal fluoride salt is a metal fluoride of titanium, zirconium and hafnium,
Specific examples include titanium tetrafluoride, titanium trifluoride, zirconium tetrafluoride, and hafnium tetrafluoride, and zirconium tetrafluoride and hafnium tetrafluoride are particularly preferred.
【００１８】使用されるフッ化水素酸アンモニウム塩の
量は４属遷移金属フッ化物塩１モルに対して、０．５〜
２．０モルで、好ましくは０．８〜１．２モルである。The amount of the ammonium hydrofluoride used is 0.5 to 1 mol of the Group 4 transition metal fluoride salt.
2.0 mol, preferably 0.8-1.2 mol.
【００１９】本発明のフッ素化反応においては、一般式
［２］で示される１−アルコキシ−２，３−エポキシ化
合物を原料とし、上記フッ素化剤を作用させて開環フッ
素化することにより、Ｃ−２選択的なフッ素化を進行さ
せ、一般式［３］に示すような、１−アルコキシ−２−
フルオロ−３−ヒドロキシ化合物を製造することができ
る。In the fluorination reaction of the present invention, a 1-alkoxy-2,3-epoxy compound represented by the general formula [2] is used as a raw material, and the above fluorinating agent is acted to effect ring-opening fluorination. C-2 Selective fluorination proceeds, and 1-alkoxy-2- as shown in general formula [3]
A fluoro-3-hydroxy compound can be produced.
【００２０】本発明における１−アルコキシ−２，３−
エポキシ化合物において、Ｒ1およびＲ2は水素、Ｃ1-10
置換または無置換の飽和または不飽和の鎖状または分岐
アルキル基、Ｃ3-8環状アルキル基、無置換もしくは置
換アリール基、無置換もしくは置換ヘテロ環を表し、同
一でも異なっていてもよい。In the present invention, 1-alkoxy-2,3-
In the epoxy compound, R 1 and R 2 are hydrogen, C 1-10
Represents a substituted or unsubstituted saturated or unsaturated chain or branched alkyl group, a C 3-8 cyclic alkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted hetero ring, which may be the same or different.
【００２１】具体的には、メチル、エチル、プロピル、
ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、デ
シル等のＣ1-10の直鎖飽和アルキル、イソプロピル、ｓ
ｅｃ−ブチル、ｔｅｒｔ−ブチル、２−メチルブチル、
イソペンチル、イソヘキシル、３−エチルオクチル等の
Ｃ1-10等の飽和分岐アルキル、ビニル、プロペニル、ブ
テニル、ペンテニル、ヘキセニル、デセニル、２−プロ
ペニル、１−メチル−１−プロペニル、１−エチル−１
−ブテニル、２，４−ジメチル−１−ペンテニル、２，
４−ジメチル−２−ペンテニル基等のＣ2-10の直鎖また
は分岐アルケニル基、シクロプロピル、シクロヘキシ
ル、シクロオクチル等のＣ3-8環状アルキル基等が挙げ
られる。 また、アリール基としては、フェニル基、ヘ
テロ環としては、ピロリジン環、ピペリジン環、、イミ
ダゾリジン環、イミダゾリジノン環、ピリミジン環、ピ
リミジノン環が挙げられる。Specifically, methyl, ethyl, propyl,
C 1-10 straight-chain saturated alkyl such as butyl, pentyl, hexyl, heptyl, octyl, decyl, isopropyl, s
ec-butyl, tert-butyl, 2-methylbutyl,
Saturated branched alkyl such as C 1-10 such as isopentyl, isohexyl and 3-ethyloctyl, vinyl, propenyl, butenyl, pentenyl, hexenyl, decenyl, 2-propenyl, 1-methyl-1-propenyl, 1-ethyl-1
-Butenyl, 2,4-dimethyl-1-pentenyl, 2,
Examples thereof include a C2-10 linear or branched alkenyl group such as a 4-dimethyl-2-pentenyl group, and a C3-8 cyclic alkyl group such as cyclopropyl, cyclohexyl, and cyclooctyl. The aryl group includes a phenyl group, and the hetero ring includes a pyrrolidine ring, a piperidine ring, an imidazolidine ring, an imidazolidinone ring, a pyrimidine ring, and a pyrimidinone ring.
【００２２】これらは置換されていてもよく、ここで置
換基としては本発明の方法において不活性な置換基であ
ればよいが、アルキル基、アルケニル基、アルキニル基
にあっては、アリール基、ヘテロ環式基、アルコキシ
基、三級アミノ基等であり、また、アーリル基、ヘテロ
環式基にあっては、アルキル基、アルケニル基、アルキ
ニル基、アリール基、ヘテロ環式基、アルコキシ基、三
級アミノ基等である。These may be substituted. The substituent may be any substituent which is inactive in the method of the present invention. In the case of an alkyl group, an alkenyl group and an alkynyl group, an aryl group, A heterocyclic group, an alkoxy group, a tertiary amino group, and the like, and, in an aryl group, a heterocyclic group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an alkoxy group, And a tertiary amino group.
【００２３】本発明のフッ素化反応に用いられるフッ素
化剤の量は、通常、一般式［２］で示される１−アルコ
キシ−２，３−エポキシ化合物に対して、１モル当量以
上使用すればよく、１〜１０モル当量が好ましく、特に
１〜５モル当量が好ましい。The amount of the fluorinating agent used in the fluorination reaction of the present invention is usually at least 1 molar equivalent relative to the 1-alkoxy-2,3-epoxy compound represented by the general formula [2]. Often, 1 to 10 molar equivalents are preferable, and particularly preferably 1 to 5 molar equivalents.
【００２４】本発明のフッ素化に用いられる反応溶媒
は、原料の１−アルコキシ−２，３−エポキシ化合物お
よび生成物である１−アルコキシ−２−フルオロ−３−
ヒドロキシ化合物と反応しないものであれば特に限定さ
れないが、例えば、アセトニトリル、プロピオニトリ
ル、ブチロニトリルのようなニトリル系、ベンゼン、ト
ルエン、キシレン、塩化ベンゼン等の芳香族類、ジエチ
ルエーテル、イソプロピルエーテル、ジブチルエーテ
ル、テトラヒドロフラン、１，４−ジオキサン等のエー
テル類、四塩化炭素、クロロホルム、ジクロロメタン等
のハロゲン化炭化水素類が挙げられる。その中でも、ア
セトニトリル、トルエン、塩化ベンゼン、テトラヒドロ
フラン、ジクロロメタンが好ましく、特にテトラヒドロ
フラン、ジクロロメタンがより好ましい。これらの溶媒
は、単独または組み合わせて使用することができる。ま
た、溶媒量は原料の１−アルコキシ−２，３−エポキシ
化合物が溶解する範囲内であればよく、使用原料量の１
倍以上用いれば良い。The reaction solvent used in the fluorination of the present invention is a 1-alkoxy-2,3-epoxy compound as a raw material and a 1-alkoxy-2-fluoro-3- as a product.
There is no particular limitation as long as it does not react with the hydroxy compound.For example, acetonitrile, propionitrile, nitriles such as butyronitrile, benzene, toluene, xylene, aromatics such as benzene chloride, diethyl ether, isopropyl ether, Ethers such as butyl ether, tetrahydrofuran, and 1,4-dioxane; and halogenated hydrocarbons such as carbon tetrachloride, chloroform, and dichloromethane. Among them, acetonitrile, toluene, benzene chloride, tetrahydrofuran, and dichloromethane are preferable, and particularly, tetrahydrofuran and dichloromethane are more preferable. These solvents can be used alone or in combination. The amount of the solvent may be within a range in which the 1-alkoxy-2,3-epoxy compound as the raw material can be dissolved.
It may be used twice or more.
【００２５】本反応のフッ素化の反応温度は、室温付近
で容易に反応が進行する。当然のことながら、加熱下に
おいては効率よく進行する。The reaction proceeds easily at a fluorination reaction temperature in the vicinity of room temperature. Naturally, the process proceeds efficiently under heating.
【００２６】本反応の後処理においては、通常の後処理
操作を行うことにより粗生成物を得ることができる。得
られた粗生成物は、必要に応じて、活性炭、蒸留、カラ
ムクロマトグラフィー等の精製操作を行うことにより、
目的の一般式［３］で示される１−アルコキシ−２−フ
ルオロ−３−ヒドロキシ化合物を得ることができる。In the post-treatment of this reaction, a crude product can be obtained by performing ordinary post-treatment operations. The obtained crude product is, if necessary, activated carbon, distillation, by performing purification operations such as column chromatography,
The desired 1-alkoxy-2-fluoro-3-hydroxy compound represented by the general formula [3] can be obtained.
【００２７】[0027]
【実施例】以下実施例により本発明の実施の形態を具体
的に説明するが、本発明はこれらの実施例に限定される
ものではない。EXAMPLES The embodiments of the present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.
【００２８】「実施例１」 ○フッ素化剤の調製 テトラブチルアンモニウム ジハイドロジェントリフル
オライド（Ｈ2Ｆ3ＮＢｕ4）と四フッ化チタン（Ｔｉ
Ｆ4）を等モル量混合し、室温で１０分間攪拌した。 ○開環フッ素化反応 フッ素化剤調製溶液（塩化ベンゼン溶液、エポキシ化合
物に対して二倍当量）に式［４］Example 1 Preparation of fluorinating agent Tetrabutylammonium dihydrogentrifluoride (H 2 F 3 NBu 4 ) and titanium tetrafluoride (Ti
F 4 ) was mixed in equimolar amounts and stirred at room temperature for 10 minutes. ○ Ring-opening fluorination reaction Formula (4) is used to prepare a fluorinating agent preparation solution (double equivalent to benzene chloride solution and epoxy compound).
【００２９】[0029]
【化７】 Embedded image
【００３０】に示す１−ヒドロキシ−２，３−エポキシ
アルコールを滴下し、０℃で１時間攪拌後、室温で８時
間攪拌した。反応は穏やかに進行し、式［５］1-Hydroxy-2,3-epoxy alcohol was added dropwise, and the mixture was stirred at 0 ° C. for 1 hour and then at room temperature for 8 hours. The reaction proceeds gently and the formula [5]
【００３１】[0031]
【化８】 Embedded image
【００３２】に示す１，３ジヒドロキシ−２−フルオロ
化合物（２−Ｆ体）をおよび式［６］The 1,3 dihydroxy-2-fluoro compound (2-F form) shown in the formula [6]
【００３３】[0033]
【化９】 Embedded image
【００３４】に示す１，２−ジヒドロキシ−３−フルオ
ロ化合物（３−Ｆ体）を得た。19Ｆ−ＮＭＲで確認した
ところ、２−Ｆ体と３−Ｆ体を合わせた収率は８６％
で、２−Ｆ体と３−Ｆ体との比は６６：３４であった。The following 1,2-dihydroxy-3-fluoro compound (3-F form) was obtained. When confirmed by 19 F-NMR, the combined yield of the 2-F form and the 3-F form was 86%.
The ratio between the 2-F form and the 3-F form was 66:34.
【００３５】「実施例２〜実施例３」実施例１と同じ系
で、フッ素化剤調製時の４属遷移金属フッ化物塩として
四フッ化チタン（ＴｉＦ4）を用い、開環フッ素化反応
時の溶媒の種類、反応時間を変えて、室温において、実
施例１と同様な操作を行った。結果を実施例１の結果と
合わせて表１に示した。"Examples 2 and 3" In the same system as in Example 1, a ring-opening fluorination reaction was carried out using titanium tetrafluoride (TiF 4 ) as a Group 4 transition metal fluoride salt when preparing a fluorinating agent. The same operation as in Example 1 was performed at room temperature by changing the type of solvent and the reaction time. The results are shown in Table 1 together with the results of Example 1.
【００３６】「実施例４〜実施例５」実施例１と同じ系
で、フッ素化剤調製時の４属遷移金属フッ化物塩として
三フッ化チタン（ＴｉＦ3）を用い、開環フッ素化反応
時の溶媒の種類、反応時間を変えて、室温において、実
施例１と同様な操作を行った。結果を表１に示した。"Examples 4 and 5" In the same system as in Example 1, a ring-opening fluorination reaction was carried out using titanium trifluoride (TiF 3 ) as a Group 4 transition metal fluoride salt when preparing a fluorinating agent. The same operation as in Example 1 was performed at room temperature by changing the type of solvent and the reaction time. The results are shown in Table 1.
【００３７】「実施例６〜実施例７」実施例１と同じ系
で、フッ素化剤調製時の４属遷移金属フッ化物塩として
四フッ化ジルコニウム（ＺｒＦ4）を用い、開環フッ素
化反応時の溶媒の種類、反応時間を変えて、室温におい
て、実施例１と同様な操作を行った。結果を表１に示し
た。[Examples 6 and 7] In the same system as in Example 1, a ring-opening fluorination reaction was carried out using zirconium tetrafluoride (ZrF 4 ) as the Group 4 transition metal fluoride salt during the preparation of the fluorinating agent. The same operation as in Example 1 was performed at room temperature by changing the type of solvent and the reaction time. The results are shown in Table 1.
【００３８】「実施例８〜実施例９」実施例１と同じ系
で、フッ素化剤調製時の４属遷移金属フッ化物塩として
四フッ化ハフニウム（ＨｆＦ4）を用い、開環フッ素化
反応時の溶媒の種類、反応時間を変えて、室温におい
て、実施例１と同様な操作を行った。結果を表１に示し
た。[Examples 8 to 9] In the same system as in Example 1, a ring-opening fluorination reaction was carried out using hafnium tetrafluoride (HfF 4 ) as a Group 4 transition metal fluoride salt when preparing a fluorinating agent. The same operation as in Example 1 was performed at room temperature by changing the type of solvent and the reaction time. The results are shown in Table 1.
【００３９】「参考例１」実施例１と同じ系で、塩化ベ
ンゼン中、フッ素化剤としてテトラブチルアンモニウム
ジハイドロジェントリフルオライド（Ｈ2Ｆ3ＮＢｕ4）
のみを使用し、１４０℃で２０時間反応させ、開環フッ
素化を行った。２−Ｆ体と３−Ｆ体を合わせた収率は６
０％で、２−Ｆ体と３−Ｆ体との比は３９：６１であっ
た。結果を表１に示した。Reference Example 1 In the same system as in Example 1, tetrabutylammonium dihydrogentrifluoride (H 2 F 3 NBu 4 ) was used as a fluorinating agent in benzene chloride.
The reaction was carried out at 140 ° C. for 20 hours to effect ring-opening fluorination. The combined yield of the 2-F form and the 3-F form is 6
At 0%, the ratio between the 2-F form and the 3-F form was 39:61. The results are shown in Table 1.
【００４０】[0040]
【表１】 [Table 1]
【００４１】[0041]
【発明の効果】１−アルコキシ−２，３−エポキシ化合
物の開環フッ素化において、Ｃ−２位選択的フッ素化生
成物を与えるフッ素化剤を簡単な操作で製造できる。According to the present invention, in the ring-opening fluorination of a 1-alkoxy-2,3-epoxy compound, a fluorinating agent giving a C-2 selective fluorination product can be produced by a simple operation.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｃ０７Ｃ 211/65 Ｃ０７Ｃ 211/65 (72)発明者 大場 志保 神奈川県横浜市戸塚区吉田町1181−７ (72)発明者 大村 浩文 神奈川県横浜市鶴見区東寺尾１−15−Ｂ５ Ｌ−502 (72)発明者 寺田 眞浩 埼玉県浦和市白幡５−13−３−102 Ｆターム(参考） 4H006 AA01 AA02 AB81 AC30 AC41 FE11 FE71 FE74 FG29 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification FI theme coat ゛ (Reference) C07C 211/65 C07C 211/65 (72) Inventor Shiho Oba 1181-7, Yoshidacho, Totsuka-ku, Yokohama-shi, Kanagawa-ken ( 72) Inventor Hirofumi Omura L-502 1-15-B5 Higashi Terao, Tsurumi-ku, Yokohama, Kanagawa Prefecture (72) Inventor Masahiro Terada 5-13-3-102, Shirahata, Urawa-shi, Saitama F-term (reference) 4H006 AA01 AA02 AB81 AC30 AC41 FE11 FE71 FE74 FG29
Claims (3)
す］で示されるフッ化水素酸アンモニウム塩と４族遷移
金属フッ化物塩とからなるフッ素化剤。1. A compound of the general formula [1] Wherein R represents a C 1-10 linear or branched alkyl group; and a fluorinating agent comprising a group 4 transition metal fluoride salt.
ニウム、ハフニウムの金属フッ化物である請求項１に記
載のフッ素化剤。2. The fluorinating agent according to claim 1, wherein the Group 4 transition metal fluoride salt is a metal fluoride of titanium, zirconium or hafnium.
の飽和または不飽和の直鎖または分岐アルキル基、Ｃ
3-8環状アルキル基、無置換もしくは置換アリール基、
無置換もしくは置換ヘテロ環を表し、同一でも異なって
いてもよい］で示される１−アルコキシ−２，３−エポ
キシ化合物に請求項１または請求項２に記載のフッ素化
剤を作用させて開環フッ素化し、一般式［３］ 【化３】 ［式中、Ｒ1およびＲ2は一般式［２］と同じ］で示され
る１−アルコキシ−２−フルオロ−３−ヒドロキシ化合
物を製造する方法。3. A compound of the general formula [2] Wherein R 1 and R 2 are hydrogen, C 1-10 substituted or unsubstituted, saturated or unsaturated, straight-chain or branched alkyl,
3-8 cyclic alkyl group, unsubstituted or substituted aryl group,
A 1-alkoxy-2,3-epoxy compound represented by an unsubstituted or substituted hetero ring, which may be the same or different, is treated with the fluorinating agent according to claim 1 or 2 to open the ring. Fluorination, general formula [3] [Wherein R 1 and R 2 are the same as those in the general formula [2]]. A method for producing a 1-alkoxy-2-fluoro-3-hydroxy compound represented by the following formula:
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