Diisobutylaluminum hydride → 2-(oxan-4-ylidene)ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

DIBAL 1 M in methylene chloride (76.9 mL, 76.9 mmol) was added to a solution of (tetrahydro-pyran-4-ylidene)-acetic acid methyl ester (4.0 g, 25.6 mmol) in methylene chloride (100 mL) under nitrogen atmosphere cooled to −78° C. The reaction was stirred for 1 h, allowed to warm to room temperature, and stirred for an additional 2 h. The reaction was cooled to 0° C. and slowly quenched with methanol (35 mL). The reaction was vigorously stirred with water (35 mL) and Na2SO4 (170 g) for 30 minutes at room temperature. The resulting slurry was filtered and concentrated to give 2-(tetrahydro-pyran-4-ylidene)-ethanol (3.2 g, 97%) as a colorless oil.

Provenance & Evidence