Cyclopentanecarbaldehyde → 1-Cyclopentylprop-2-yn-1-ol

Participants

Reaction Steps

A solution of 0.87 ml of cyclopentanecarboxaldehyde (8.15 mmol; Aldrich) in 10 ml of tetrahydrofuran is added to 18 ml of a commercially available 0.5 M solution of ethynylmagnesium bromide in tetrahydrofuran (10 mmol, Aldrich) cooled beforehand to 0° C. The mixture is then stirred for 2 hours at ambient temperature and a saturated solution of NH4Claq is added. The mixture is extracted with ethyl acetate and the organic phases are then combined, washed with a saturated solution of NaClaq, dried over sodium sulphate, filtered, and concentrated under vacuum. 0.931 g of (±)-1-cyclopentylprop-2-yn-1-ol is obtained in the form of a light brown oil with a yield of 92%.

Provenance & Evidence