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

Temperature

0 °C

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)−.

1. temperatureThe resulting suspension was heated
2. temperatureto reflux for 3 h
3. customcautiously quenched with water (2 mL)
4. concentrationconcentrated to dryness in vacuo
5. additionWater (20 mL) was added to the residue
6. temperaturethe mixture was cooled to 0° C.
7. customThe solids were removed by filtration
8. washwashed with water
9. customto air-dry
10. customRecrystallization from water

ORD record

ord-fb6a658dbbcc479a82d24892a74aa792

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06825170B2