Aluminium lithium hydride → [4-[(1E)-3-hydroxy-1-propenyl]phenyl]boronic Acid

Participants

Reaction Conditions

Reaction Steps

Lithium aluminum hydride (1.0 M solution in THF, 19.0 mL, 19.0 mmol) was added dropwise over 10 min to a solution of [4-(3-hydroxy-1-propynyl)phenyl]boronic acid (1.06 mg, 6.02 mmol, prepared as described in Reference Example 235) in THF (50 mL) with vigorous strirring. The resulting suspension was heated to reflux for 3 h, cooled to 0° C., cautiously quenched with water (2 mL), strirred for 10 min, and concentrated to dryness in vacuo. Water (20 mL) was added to the residue, the mixture was cooled to 0° C., acidified with 20% H2SO4 (10 mL), and stirred for 10 min at 0° C. The solids were removed by filtration, washed with water, and allowed to air-dry. Recrystallization from water provided 0.70 g (69%) of the title compound as colorless crystals. MS 177 (M−H)−.

Provenance & Evidence