反応 #1005976

反応方程式

2,2-dimethyl-4-oxo-thiochroman-6-yl trifluoromethanesulfonate

trimethylsilylacetylene

→

2,2-dimethyl-6-trimethylsilanylethynyl-thioc-hroman-4-one

収率 91.0%

溶媒

Et3N

DMF

H2O

反応条件

後処理

1. 1
   温度cooled to room temperature
2. 2
   抽出Extraction with EtOAc
3. 3
   洗浄by washing the combined organic layers with H2O and saturated aqueous NaCl
4. 4
   乾燥drying over MgSO4

実験手順

A solution of 2,2-dimethyl-4-oxo-thiochroman-6-yl trifluoromethanesulfonate (2.88 g, 8.50 mmol) in 10 mL Et3N and 20.0 mL DMF was purged with argon for 10 minutes. To this solution was added trimethylsilylacetylene (4.15 g, 42.0 mmol) and bis(triphenylphosphine)-palladium (II) chloride (298.0 mg, 0.425 mmol). The solution was heated to 95° C. for 5 hours, cooled to room temperature, and diluted with H2O. Extraction with EtOAc was followed by washing the combined organic layers with H2O and saturated aqueous NaCl and drying over MgSO4. Concentration of the dry solution under reduced pressure and isolation of the product by column chromatography (3% EtOAc/hexanes) afforded 2.23 g (91%) of the 2,2-dimethyl-6-trimethylsilanylethynyl-thioc-hroman-4-one as an orange oil. 1H NMR (300 MHz, CDCl3) δ: 8.18 (1H, d, J=1.9 Hz), 7.34 (1H, dd, J=1.9, 8.1 Hz), 7.15 (1H, d, J=8.1 Hz), 2.85 (2H, s), 1.45 (6H, s), 0.23 (9H, s).

出典