6-Carbomethoxymethyl-6-ethyl-2-cyclohexen-1-one → 1-Ethyl-2-hydroxy-3-cyclohexeneethanol

Participants

Reaction Steps

A solution of 1-ethyl-2-oxocyclohex-3-eneacetic acid methyl ester (5.00 g, 25.48 mmol) in 10 mL of anhydrous ether was added dropwise under nitrogen to a 0° C. solution of lithium aluminum hydride (967 mg, 25.48 mmol) in 25 mL of anhydrous ether. The reaction was quenched by dropwise addition of 0.97 mL of water, 0.97 mL of 1M NaOH (aqueous) and 2.7 mL of water. The solution was filtered and the salts were boiled 3× in 25 mL of ethyl acetate and these washings were combined with the first filtrate. The filtrate was concentrated in vacuo to afford 4.47 g (103%) of product as a colorless oil.

Provenance & Evidence