GB1259675A - Substituted aldehydes - Google Patents

Substituted aldehydes

Info

Publication number
GB1259675A
GB1259675A GB18719/71A GB1871971A GB1259675A GB 1259675 A GB1259675 A GB 1259675A GB 18719/71 A GB18719/71 A GB 18719/71A GB 1871971 A GB1871971 A GB 1871971A GB 1259675 A GB1259675 A GB 1259675A
Authority
GB
United Kingdom
Prior art keywords
tetrahydropyran
acetyl
hydroxy
yloxy
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB18719/71A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth LLC
Original Assignee
American Home Products Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Home Products Corp filed Critical American Home Products Corp
Priority claimed from GB1601/69A external-priority patent/GB1259673A/en
Publication of GB1259675A publication Critical patent/GB1259675A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C07C59/215—Saturated compounds having only one carboxyl group and containing keto groups containing singly bound oxygen containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C07C59/225—Saturated compounds having only one carboxyl group and containing keto groups containing —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,259,675. 2,3 - Disubstituted - levulinaldehydes. AMERICAN HOME PRODUCTS CORP. 10 Jan., 1969 [1 Feb., 1968; 4 Oct., 1968], No. 18719/71. Divided out of 1,259,673. Heading C2C. Novel 2,3 - disubstituted - levulinaldehydes of the formula wherein R<SP>1</SP> is 6-carboxyhexyl or 6-carbo- (C 1-7 alkoxy)hexyl and R<SP>2</SP> is 3-hydroxyoctyl or R<SP>1</SP> is 6-carboxyhexyl or 6-carbonethoxyhexyl and R<SP>2</SP> is 3-tetrahydropyran-2<SP>1</SP>-yloxyoctyl or R<SP>1</SP> is 6-carbethoxyhexyl and R<SP>2</SP> is 3-acetoxyoctyl are prepared by ozonizing the appropriate 1,3,4-trisubstituted-hex-1-ene of the formula when R is, for example, CH 3 and decomposing the resulting ozonide. Compounds in which R<SP>2</SP> is 3-hydroxyoctyl may be obtained by hydrolysing the corresponding compounds in which R<SP>2</SP> is 3 - tetrahydropyran - 2<SP>1 </SP>- yloxyoetyl. 8 - Acetyl - 12 - (tetrahydropyran - 2 - yloxyoxy)- 9 - (1 - propenyl)heptadecanoic acid methyl ester (I) is prepared from hexanal (II) by the following reaction sequence: I#oct - 1 - yn - 3 - ol # 2 - (oct - 1 - yn - 3 - yloxy)tetrahydropyran # 4 - (tetrahydro - pyran - 2 - yloxy) - 2- nonynal; diethyl acetal # 4 - hydroxy - 2- nonynal # 4 - (tetrahydropyran - 2 - yl - oxy)- 2 - nonynal # 4 - (tetrahydropyran - 2 - yloxy)- nonanal # 7 - (tetrahydropyran - 2 - yloxy) - 2- dodecyn - 4 - ol # 7 - (tetrahydropyran - 2- yloxy) - 2 - dodecyn - 4 - ol, methane sulphonate # 2 - acetyl - 2 - [1 - (1 - propynyl) - 4 - (tetrahydropyran - 2 - yloxy)nonyl] - nonanedioic acid, 1 - t - butyl ester, 9 - ethyl ester # 2 - acetyl - 2- [4 - hydroxy - 1 - (1 - propynyl) - nonyl]nonanedioic acid, 1 - t - butyl, 9 - ethyl ester # 2- acetyl - 2 - [4 - hydroxy - 1 - (1 - propynyl)nonyl]- nonanedioic acid, 1 - t - butyl, 9 - ethyl ester, acetate # 2 - acetyl - 2 - [4 - hydroxy - 1 - (1- propenyl) nonyl] nonanedioic acid, 1 - t - butyl ester, 9 - ethyl ester, acetate#8-acetyl - 12- hydroxy - 9 - (1 - propenyl)heptadecanoic acid, ethyl ester, acetate # 8 - acetyl - 12 - hydroxy- 9 - (1 - propenyl)heptadecanoic acid # 8- acetyl - 12 - hydroxy - 9 - (1 - propenyl)heptadecanoic acid, methyl ester # I. 2 - Acetylnonadioic acid, 1 - t - butyl ester, 9- ethyl ester is obtained by reacting t-butyl acetoacetate with sodium hydride and condensing the resulting anion formed thereby with ethyl 7- bromo-heptanoate.
GB18719/71A 1968-02-01 1969-01-10 Substituted aldehydes Expired GB1259675A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US70218568A 1968-02-01 1968-02-01
US76502068A 1968-10-04 1968-10-04
GB1601/69A GB1259673A (en) 1968-02-01 1969-01-10 Substituted cyclopentanones

Publications (1)

Publication Number Publication Date
GB1259675A true GB1259675A (en) 1972-01-12

Family

ID=27253916

Family Applications (2)

Application Number Title Priority Date Filing Date
GB18718/71A Expired GB1259674A (en) 1968-02-01 1969-01-10 Substituted cyclopentanones
GB18719/71A Expired GB1259675A (en) 1968-02-01 1969-01-10 Substituted aldehydes

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB18718/71A Expired GB1259674A (en) 1968-02-01 1969-01-10 Substituted cyclopentanones

Country Status (1)

Country Link
GB (2) GB1259674A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097504A (en) * 1975-04-23 1978-06-27 Merck & Co., Inc. 11,12-Secoprostaglandins

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097504A (en) * 1975-04-23 1978-06-27 Merck & Co., Inc. 11,12-Secoprostaglandins

Also Published As

Publication number Publication date
GB1259674A (en) 1972-01-12

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees