Reaction #2254185

Reaction equation

MTBE

LiH

3′,5′-dichloro-2,2,2-trifluoroacetophenone

1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone

→

3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-one

Yield 56.1%

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONthe reaction mixture is poured onto water (30 ml) at 5° C
2. 2
   ExtractionThe organic phase is extracted with water
3. 3
   Dryinga saturated aqueous solution of NaCl, dried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo

Procedure

LiH (1.72 g) is added to a solution of 3′,5′-dichloro-2,2,2-trifluoroacetophenone (26.6 g) and 1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone (18.2 g) in THF (100 ml). After 30 minutes at 60° C. MTBE is added (200 ml) and the reaction mixture is poured onto water (30 ml) at 5° C. The organic phase is extracted with water and a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield 3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-one (20.7 g). The crude product is used without further purification.

Source