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 methanol (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 adding 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 ethyl acetate (200 mL). The organic layer was separated and the aqueous layer extracted with ethyl acetate (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% ethyl acetate 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
2. additionby adding 2 M hydrochloric acid (50 mL)
3. customThe volatile materials were removed
4. concentrationby concentrating on a rotary evaporator
5. customthe residue partitioned between water (100 mL) and ethyl acetate (200 mL)
6. customThe organic layer was separated
7. extractionthe aqueous layer extracted with ethyl acetate (2×200 mL) The combined organic extracts
8. washwere washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated to dryness

ORD record

ord-c37e887558f2490c9a6355bc2db8c923

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423067B2