反应详情

温度

-78 °C

n-Butyllithium (1.53 g, 24 mmol) in hexane (9.5 mL) was added dropwise to a stirred solution of 2-methyl-4,5-diphenylthiazole (5 g, 20 mmol) in dry THF (150mL,) maintained at -78° C. under an atmosphere of nitrogen. After 25 minutes a solution of [3-(bromomethyl)phenoxy]dimethyl(1,1-dimethylethyl)silane (6.60 g, 22mmol) in THF (10mL) was added dropwise, the mixture stirred at -78° C. for 10 minutes and the allowed to warm to room temperature. The reaction mixture was poured onto saturated ammonium chloride solution, extracted with CH2Cl2, the extracts combined, dried over sodium sulfate and concentrated in vacuo to leave an oil which was dissolved in THF (25 mL). A solution of tetra-n-butylammonium fluoride (6.77 g, 26 mmol) in THF (25.86 mL) was added and the mixture stirred at room temperature for 30 minutes before being diluted with 1N HCl solution (100 mL). The mixture was extracted with CH2Cl2, the combined extracts dried over sodium sulfate and concentrated to leave an oil. Chromatography on a column of silica gel using a mixture of hexanes and diethyl ether (2:1) as eluent furnished 3-[2-(4,5-diphenyl-2-thiazolyl)ethyl]phenol (4.13 g, 58%), mp 166°-168° C. after recrystallization from a mixture of hexanes and CH2Cl2.

1. temperatureto warm to room temperature
2. extractionextracted with CH2Cl2
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customto leave an oil which
6. stirringthe mixture stirred at room temperature for 30 minutes
7. extractionThe mixture was extracted with CH2Cl2
8. dry with materialthe combined extracts dried over sodium sulfate
9. concentrationconcentrated
10. customto leave an oil