反应详情

温度

-110 °C

To a solution of 20.0 g (82.9 mmol) of 4-bromo-2-methyl-methoxyindane in 200 ml of THF 33.2 ml of 2.5 M (83.0 mmol) n-BuLi in hexanes was added for 20 min at −80° C. This mixture was stirred for 40 min at this temperature, cooled to −110° C., and 4.38 g (99.4 mmol) of ethylene oxide was added by one portion at vigorous stirring. The resulting mixture was stirred for 12 h at room temperature, and then 10 ml of water was added. The organic layer was separated and evaporated to dryness. To the residue 200 ml of water was added, and the crude product was extracted with 3×100 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography using short column with Silica Gel 60 (40-63 um, d 110 mm, 190 mm; eluent: hexanes/ether=20/1). Yield 12.7 g (74%) of a ca. 1 to 1.2 mixture of two diastereomers.

1. stirringThe resulting mixture was stirred for 12 h at room temperature
2. customThe organic layer was separated
3. customevaporated to dryness
4. additionTo the residue 200 ml of water was added
5. extractionthe crude product was extracted with 3×100 ml of dichloromethane
6. extractionThe combined organic extract
7. dry with materialwas dried over Na2SO4
8. customevaporated to dryness
9. customThe product was isolated by flash chromatography
10. additionYield 12.7 g (74%) of a ca. 1 to 1.2 mixture of two diastereomers