Cycloheptanecarboxylic acid → Cycloheptanemethanol

Temperature

0 °C

To an ice-cold solution of cycloheptane carboxylic acid (83 g, 0.58 mol) in THF (350 mL) was added BH3-THF (700 mL of a 1M solution in THF, 0.70 mol) dropwise. The reaction mixture was stirred at 0° C. for 30 min. After warming to room temperature, the reaction was quenched with the addition of MeOH (300 mL) initially dropwise then more quickly. The mixture was concentrated under reduced pressure. The residue was partitioned between EtOAc and aqueous NaHCO3, washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by distillation (96° C. at 19 Torr) gave pure cycloheptylmethanol. Yield (58.3 g, 78%). 1H NMR (DMSO-d6) δ 4.36 (dt, J=3.5, 1.9 Hz, 1H), 3.13 (t, J=6.0 Hz, 2H), 1.34-1.69 (m, 11H), 1.02-1.10 (m, 2H).

1. temperatureAfter warming to room temperature
2. customthe reaction was quenched with the addition of MeOH (300 mL) initially dropwise
3. concentrationThe mixture was concentrated under reduced pressure
4. customThe residue was partitioned between EtOAc and aqueous NaHCO3
5. washwashed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated under reduced pressure
8. customPurification
9. distillationby distillation (96° C. at 19 Torr)

ORD record

ord-4da7f143332a4a4e9ebfaddf9ad8908e

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08981153B2