Water → 2-[4-[(3,5-Dichlorophenyl)sulfanyl]-5-ethyl-3-(hydroxymethyl)-1H-pyrazol-1-yl]ethanol

Temperature

-78 °C

A solution of Example 46 (65 mg, 0.17 mmol) in tetrahydrofuran (2.5 ml) was cooled to −78° C. and treated with lithiumaluminium hydride (1M in THF) (170 μL, 0.17 mmol). After stirring at −78° C. for 2 hours the reaction mixture was allowed to warm to 0° C. for 1 hour and was then allowed to warm to room temperature. After stirring at this temperature for 18 hours, water (1 ml) was added. The reaction mixture was partitioned between ethyl acetate (25 ml) and water (25 ml). The organic phase was dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume) to afford the title compound (42 mg) as a colourless oil, which solidified on standing, m.p. 89–90° C.

1. temperatureto warm to 0° C. for 1 hour
2. temperatureto warm to room temperature
3. stirringAfter stirring at this temperature for 18 hours
4. customThe reaction mixture was partitioned between ethyl acetate (25 ml) and water (25 ml)
5. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude material was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume)

ORD record

ord-452775bf55dc466ab65ff2fc88652d7c

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141585B2