Water → 3,4-Dihydro-2,5-dimethyl-2H-pyran-2-methanol

Participants

Reaction Steps

3.12 g of sodium borohydride was added to a rapidly stirred mixture of 140 ml of ether and 70 ml of water under a nitrogen atomosphere. To the resulting solution, a solution of 21.0 g of 3,4-dihydro-2,5-dimethyl-2H-pyran-2-carboxaldehyde (U.S. Pat. No. 2,479,283) in 42 ml of ether was added drop by drop. After 30 minutes, 21 ml of acetone was added. After 5 more minutes, the mixture was doubled in volume with a saturated solution of potassium carbonate and extracted with ether. The extract was washed with saturated sodium chloride solution, dried (sodium sulfate) and stripped of solvent to give 3,4-dihydro-2,5-dimethyl-2H-pyran-2-methanol (12A), as a pale green liquid, b.p.: not determined.

Provenance & Evidence