4-(4-chlorophenyl)-3-phenyl-2-Butanone → 4-(4-Chlorophenyl)-3-phenyl-2-butanol

Temperature

0 °C

To a solution of 4-(4-chlorophenyl)-3-phenyl-2-butanone (Step D, 13 g, 50 mmol) in MeOH (100 mL) at 0° C. was added sodium borohydride (3.8 g, 100 mmol). After stirring at 0° C. for 30 min, the reaction was quenched by addition of 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between water (100 mL) and EtOAc (200 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the crude product, which was purified by flash column chromatography on silica gel eluted with 10% EtOAc in hexane to afford the pure faster eluting isomer and a mixture containing both the faster eluting isomer and the slower eluting isomer. Faster eluting isomer: 1H NMR (500 MHz, CD3OD): δ 7.25-7.00 (m, 9H), 4.00 (m, 1H), 3.15 (m, 1H), 2.97 (m, 1H), 2.85 (m, 1H), 1.10 (d, 3H).

1. customthe reaction was quenched by addition of 2 M hydrochloric acid (50 mL)
2. customThe volatile materials were removed
3. concentrationby concentrating on a rotary evaporator
4. customthe residue partitioned between water (100 mL) and EtOAc (200 mL)
5. customThe organic layer was separated
6. extractionthe aqueous layer extracted with EtOAc (2×200 mL)
7. washThe combined organic extracts were washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated to dryness

ORD record

ord-2f70beb27aff45bd805b5d885df38187

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06972295B2