反应详情

温度

0 °C

To a suspension of 60.0 g of 3-(tert-butyldimethylsilyloxymethyl)bromobenzene (prepared from tert-butyldimethylchlorosilane and 3-bromobenzyl alcohol according to the procedure described by Kendall P. M. et al., J. Org. Chem., 1979, 44, 1421) in 500 ml of anhydrous THF cooled to -78° C., 131 ml of 1.6M n-butyllithium in n-hexane were added under a nitrogen atmosphere and the resulting mixture was stirred for 2.5 hrs. A solution of 6.30 g of (1S,3aS,7aR)-1-hydroxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone in 60 ml of anhydrous THF was added. After 1 hr the reaction mixture was allowed to warm to 0° C., and cautiously quenched with 300 ml of 5% aqueous NaH2PO4.H2O and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) with n-hexane/acetone/chloroform 6:2:2 as the eluant to give 9.62 g of (1S,3aS,5R,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxymethylphenyl)-7a-methylperhydroinden-3a,5-diol as a white foam.

1. waitAfter 1 hr the reaction mixture was allowed
2. customcautiously quenched with 300 ml of 5% aqueous NaH2PO4.H2O
3. extractionextracted with ethyl acetate
4. dry with materialThe organic layer was dried over sodium sulfate
5. customevaporated to dryness under reduced pressure
6. customThe residue was purified by flash-chromatography (SiO2) with n-hexane/acetone/chloroform 6:2:2 as the eluant