反应详情

To a stirred solution of 8-(thiophene-2-yl)octyl magnesium bromide [0.62 mmol, prepared from 1-bromo-8-(thiophen-2-yl)octane; 0.170 g, 0.620 mmol and 1.24 mmol magnesium with a catalytic amount of 1,2 dibromoethane as initiator] in tetrahydrofuran (2 ml) at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.104 g, 0.620 mmol) in tetrahydrofuran (3 ml). The solution was warmed to room temperature, stirred for one hour, quenched with saturated ammonium chloride solution and extracted into ethyl ether. The organic portion was washed with saturated sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to a yellow oil. Purification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane) gave the desired alcohol.

1. customquenched with saturated ammonium chloride solution
2. extractionextracted into ethyl ether
3. washThe organic portion was washed with saturated sodium bicarbonate solution, water, saturated sodium chloride solution
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated to a yellow oil
7. customPurification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane)