反応 #588684

反応方程式

2,4-Difluoroacetophenone

4-{3-[(triisopropylsilyl)thio]phenyl}-tetra-hydro-2H-pyran-4-carboxamide

tetrabutylammonium fluoride

potassium tert-butoxide

HCl

→

4-{3-[(4-acetyl-3-fluorophenyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide

溶媒

toluene

ethyl acetate

反応条件

後処理

1. 1
   温度The mixture was warmed to 90 degrees Celcius
2. 2
   workup.STIRRINGThe mixture was then stirred for 30 minutes
3. 3
   ろ過a beige precipate was collected by suction filtration
4. 4
   その他The crude product was purified further on silica gel eluting with a 70:30 mixture of methylene chloride and acetone
5. 5
   濃縮The appropriate fractions were concentrated to a light brown solid, (0.61 g, 64%)

実験手順

2,4-Difluoroacetophenone (0.40 g, 2.54 mmols), 4-{3-[(triisopropylsilyl)thio]phenyl}-tetra-hydro-2H-pyran-4-carboxamide (1.0 g, 2.54 mmols), tetrabutylammonium fluoride (0.66 g, 2.54 mmols), and potassium tert-butoxide (1.0 M in THF, 2.54 ml, 2.54 mmols) were added to anhydrous toluene (10 ml). The mixture was warmed to 90 degrees Celcius and stirred for 4 hours. After cooling to room temperature, ethyl acetate was added (100 ml) along with 1.0 N HCl (6 ml). The mixture was then stirred for 30 minutes and a beige precipate was collected by suction filtration. The crude product was purified further on silica gel eluting with a 70:30 mixture of methylene chloride and acetone. The appropriate fractions were concentrated to a light brown solid, (0.61 g, 64%).

出典