反应详情

n-Butyl lithium (a 1.6M solution in hexane; 0.56 ml, 0.94 mmol) was added dropwise to a solution of (2-naphthyl)propyl tributylstannylmethyl ether (437 mg, 0.89 mmol), prepared as in Example 3, in tetrahydrofuran (5 ml) at -78° under argon. After 5 minutes, a solution of 5-trimethylsilyl-3-furaldehyde (150 mg, 0.89 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued at -78° for 2 hours and at room temperature for 1 hour. The mixture was quenched with water and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 30% ethyl ether/hexane. The title alcohol was obtained as a colorless oil.

1. waitwas continued at -78° for 2 hours and at room temperature for 1 hour
2. customThe mixture was quenched with water
3. extractionextracted with ethyl ether
4. customEvaporation of the
5. dry with materialdried (magnesium sulphate)
6. customextracts gave an oil, which
7. customchromatographed on silica using 30% ethyl ether/hexane