Water → HCID 59608877, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 52.77 g (196.0 mmol) of 4-bromo-1-methoxy-2,5,6-trimethylindane in 300 ml of THF 156.8 ml of 2.5 M (392.1 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 17.27 g (392.1 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, l 90 mm; eluent: hexanes/ether=20/1). Yield 36.66 g (80%) of a ca. 1 to 1.7 mixture of two diastereomers.

Provenance & Evidence