Реакция #1005976

Уравнение реакции

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

trimethylsilylacetylene

→

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

Выход 91.0%

Растворители

Et3N

DMF

H2O

Условия реакции

Обработка

1. 1
   Температураcooled to room temperature
2. 2
   ЭкстракцияExtraction with EtOAc
3. 3
   Промывкаby washing the combined organic layers with H2O and saturated aqueous NaCl
4. 4
   Сушкаdrying over MgSO4

Методика

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).

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