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

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Reaction Steps

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).

Provenance & Evidence