Diethyl propylmalonate → 2-[2-(2-Hydroxyethyl)-4-methoxycyclohexylmethyl]-valeric acid

HRID 745749Notes

Reaction equation

HRID 745749 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][OH:13].[CH2:14]([CH:17]([C:23](OCC)=O)[C:18]([O:20]CC)=[O:19])[CH2:15][CH3:16]>>[OH:13][CH2:12][CH2:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[CH2:2][CH:17]([CH2:14][CH2:15][CH3:16])[C:18]([OH:20])=[O:19].[OH:13][CH2:12][CH2:11][CH:4]1[CH2:5][CH:6]([O:9][CH3:10])[CH2:7][CH2:8][CH:3]1[CH2:23][CH:17]([CH2:14][CH2:15][CH3:16])[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 16552Diethyl propylmalonateHCID 233119122-(2-Chloromethyl-5-methoxyphenyl)-ethanol

Product 2

HCID 233118962-[2-(2-Hydroxyethyl)-4-methoxycyclohexylmethyl]-valeric acidHCID 233119082-[2-(2-Hydroxyethyl)-4-methoxybenzyl]-valeric acid

Procedure

2-Cyano-2-propyl-6-methoxy-trans-decalin is obtained analogously from 2-(2-bromoethyl-4-methoxycyclohexylmethyl)-valeronitrile (obtainable by chloromethylation of 2-(m-methoxyphenyl)-ethanol to give 2-(2-chloromethyl-5-methoxyphenyl)-ethanol, reaction with diethyl propylmalonate, hydrolysis and decarboxylation to give 2-[2-(2-hydroxyethyl)-4-methoxybenzyl]-valeric acid, hydrogenation to 2-[2-(2-hydroxyethyl)-4-methoxycyclohexylmethyl]-valeric acid, conversion into the amide, reaction with SOBr2 to give 2-(2-bromoethyl-4-methoxy-cyclohexylmethyl)-valeramide and dehydration).

Workup

  1. customto give

Sources & evidence

ORD record
ord-9fbd802e79fa43318ab9d12c3013da92
Source dataset
uspto-grants-1986_07
Patent number
US04600528

Reaction notes

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