Реакция #43922

Уравнение реакции

hydrochloric acid

3′-fluoro-2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde

methanol

sodium borohydride

→

title compound

Выход 94.0%

{3′-fluoro-2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol

Выход 94.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураcooled
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ПромывкаThe extract was washed with saturated brine
4. 4
   Сушкаdried over anhydrous magnesium sulfate
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-80:20)
7. 7
   Другоеthe obtained crystals were recrystallized from heptane-ethyl acetate

Методика

A solution of 3′-fluoro-2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (2.77 g, 8.00 mmol) in a mixed solvent of methanol (10 mL) and tetrahydrofuran (20 mL) was ice-cooled, sodium borohydride (90%, 0.336 g, 8.00 mmol) was added, and the mixture was stirred for 8 hr under nitrogen atmosphere. The reaction mixture was treated with diluted hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-80:20), and the obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (2.75 g, yield 94%) as colorless crystals.

Источник