Sodium borohydride → (2,2-Dimethyloxan-4-yl)methanol

Participants

Reaction Steps

A solution of 2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde (2.5 g) in ethanol (30 mL) was cooled (ice bath) and sodium borohydride (665 mg) was added with stirring. The ice bath was removed and the mixture was allowed to warm to room temperature. After 2 h the reaction was heated to 50° C. for 1 h, then allowed to cool to room temperature. The solvent was evaporated and the residue was treated with brine, acidified and extracted into DCM (×3). The combined organics were dried through a hydrophobic frit and evaporated to give a clear oil (2.54 g).

Provenance & Evidence