Sodium borohydride → ethyl (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionate

To a suspension (30 ml) of zinc chloride (2.70 g, 19.84 mmol) in ether was added sodium borohydride (1.50 g, 39.68 mmol) at room temperature and the mixture was stirred as it was for 2 hrs. Insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-(3-chlorophenyl)-3-oxo-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionate (4.45 g, 9.92 mmol) in ether (20 ml), and the mixture was stirred at room temperature for 1 hr. The reaction was quenched with 1N hydrochloric acid. The mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, 5:1) to give ethyl (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionate (3.95 g, 89%) as a colorless transparent oil.

1. filtrationInsoluble material was filtered off
2. stirringthe mixture was stirred at room temperature for 1 hr
3. customThe reaction was quenched with 1N hydrochloric acid
4. additionThe mixture was diluted with ethyl acetate
5. washwashed with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, 5:1)

ORD-Eintrag

ord-ad1a727f69354d0dadbf3a5c808338eb

Quelldatensatz

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06982348B2