Sodium borohydride → HCID 59300672, compound

Temperature

0 °C

Aldehyde 31.2 (162 mg, 0.574 mmol) was dissolved in MeOH (6 mL) and cooled to 0° C. Sodium borohydride (22.0 mg, 0.574 mmol) was added to the reaction. The solution was allowed to slowly warm to room temperature and was stirred for 1.5 hours. The reaction was quenched with dilute hydrochloric acid and then concentrated to dryness under reduced pressure. Water (20 mL) was added to the residue, and the mixture was extracted with EtOAc (2×50 mL). The organic layers were combined, washed with brine (1×30 mL), and dried over magnesium sulfate. The filtrate was concentrated to give 31.3 (151 mg). 1H NMR (400 MHz, CDCl3) δ ppm 7.38-7.43 (3 H, m), 7.27-7.32 (3 H, m), 7.20 (2 H, d, J=8.2 Hz), 4.61 (2 H, s).

1. temperatureto slowly warm to room temperature
2. customThe reaction was quenched with dilute hydrochloric acid
3. concentrationconcentrated to dryness under reduced pressure
4. additionWater (20 mL) was added to the residue
5. extractionthe mixture was extracted with EtOAc (2×50 mL)
6. washwashed with brine (1×30 mL)
7. dry with materialdried over magnesium sulfate
8. concentrationThe filtrate was concentrated

ORD record

ord-ed296349abde4ddc88ac4bce4ebf92df

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003648B2