Ammonium Chloride → (4-Bromo-5-methylthiophen-2-yl)methanol

A solution of the compound (1.00 g) obtained in Example 126a in ethanol (20 mL) was cooled in an ice bath, and sodium borohydride (0.28 g) was added. The reaction mixture was stirred at room temperature for 1 hr and cooled in an ice bath. Aqueous saturated ammonium chloride was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with aqueous saturated ammonium chloride and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (0.79 g) as an oil.

1. temperaturecooled in an ice bath
2. extractionthe mixture was extracted with ethyl acetate
3. washThe ethyl acetate layer was washed successively with aqueous saturated ammonium chloride and saturated brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

ORD record

ord-f3b332616c4b44f489f65603afe8ed8e

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461348B2