Water → HCID 69825517, compound

Participants

Reaction Steps

A solution of ethyl 5-cyclopentyl-3-methylpent-4-enoate (16.8 g; 80 mmol; obtained according to Streinz, L., Romanuk, M., Sorm, F., Sehnal, F. DE 2 444 837, priority 20.09.1973) in diethyl ether (30 ml) was added dropwise to a suspension of lithium aluminum hydride (3.0 g; 80 mmol) in the same solvent (110 ml), and the reaction mixture was stirred at reflux for 1 hour. Water (3.5 ml), then 15% NaOH solution, and again water (3.5 ml) were added, the precipitate filtered off and washed with MTBE (30 ml). The combined organic phases were washed with 1 N HCl (200 ml) and brine (3×100 ml), dried (MgSO4), concentrated in vacuo, and distilled (79-82° C./0.07 torr) to give 7.8 g (59% yield) of 5-cyclopentyl-3-methylpent-4-en-1-ol.

Provenance & Evidence