反应详情

Sodium hydride (2.13 g of a 50% dispersion in mineral oil, 44 mmol) was washed twice with hexanes, covered with dry THF (150 mL) and 1-benzoylacetone (6.00 g, 37 mmol) added portionwise. The mixture was stirred at room temperature under an atmosphere of nitrogen for 10 minutes to give a slurry which was cooled to -20° C. n-Butyllithium (2.60 g, 40 mmol) in hexane (16.3 mL) was added dropwise to provide a solution which was stirred for 20 minutes prior to the dropwise addition of [3-(bromomethyl)phenoxy]dimethyl(1,1-dimethylethyl)silane (11.17 g, 37 mmol). After 15 minutes, the mixture was poured onto saturated ammonium chloride solution and extracted with CH2Cl2. The combined extracts were dried over sodium sulfate, concentrated in vacuo and the residual oil chromatographed on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (9:1) gave 5-[3-[dimethyl(1,1-dimethylethyl)siloxy]phenyl]-1-phenyl- 1,3-pentanedione (9.00 g, 63%).

1. washSodium hydride (2.13 g of a 50% dispersion in mineral oil, 44 mmol) was washed twice with hexanes
2. additionadded portionwise
3. customto give a slurry which
4. additionwas added dropwise
5. customto provide a solution which
6. stirringwas stirred for 20 minutes
7. waitAfter 15 minutes
8. extractionextracted with CH2Cl2
9. dry with materialThe combined extracts were dried over sodium sulfate
10. concentrationconcentrated in vacuo
11. customthe residual oil chromatographed on a column of silica gel
12. washElution
13. additionwith a mixture of hexanes and diethyl ether (9:1)