Diethyl Ether → HCID 76099180, compound

Participants

Reaction Conditions

Reaction Steps

To 2.38 ml (0.017 mol) diisopropylamine in 10 ml tetrahydrofuran at -78° C. was added dropwise 6.17 ml (0.015 mol) 2.5M butyllithium in hexanes. The reaction mixture was warmed in -20° C. and then cooled back to -78° C. To this solution was added dropwise 5.0 g (0.015 mol) 2-endo-(+/-)-5-methyl-2-[[[(4-methylphenyl)sulfonyl]oxy]-methyl]-6-oxabicyclo[3.2.1]-octan-4-one in 10 ml tetrahydrofuran. The reaction mixture was allowed to warm to ambient temperature and stirred for four hours. The reaction was cooled to 0° C. and 50 ml of isopropanol was added. Ether was added and organic layer was washed with water, dried over MgSO4, filtered, and concentrated to an oil. Flash chromatography in 20:1 hexanes:ethylacetate, followed by 6:1 hexanes:ethylacetate yielded 1.32 g of oil.

Provenance & Evidence