反应详情

31 mg (0.160 mmol) of CuI was added under argon to a degassed solution of 2:225 g (8.000 mmol) of 2-(4-iodo-2-methylphenoxy)ethanol, 1.22 mL (8.80 mmol) of trimethylsilylacetylene, 185 mg (0.160 mmol) of tetrakis(triphenylphosphane)palladium, and 2.38 mL (24.00 mmol) of piperidine in 50 mL of THF and the mixture was stirred for 1 hour at RT. The reaction mixture was diluted with water and the aqueous phase was exhaustively extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl solution, dried over sodium sulfate, and evaporated down in vacuo. Purification of the crude product by column chromatography (silica gel, cyc/EtOAc 2:1) yielded light brown crystals. Yield: 1.70 g (86% of theoretical); C14H20O2Si (M=248.393); calc.: molpeak (M+H)+: 249; found: molpeak (M+H)+: 249; Rf value: 0.24 (silica gel, cyc/EtOAc 2:1).

1. extractionthe aqueous phase was exhaustively extracted with EtOAc
2. washThe combined organic phases were washed with saturated aqueous NaCl solution
3. dry with materialdried over sodium sulfate
4. customevaporated down in vacuo
5. customPurification of the crude product by column chromatography (silica gel, cyc/EtOAc 2:1)
6. customyielded light brown crystals