Ethylene Oxide → 2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5-(2-hydroxyethyl)furan

Participants

Reaction Conditions

Reaction Steps

t-BuLi (1.2 M in pentane, 10 mL, 16.99 mmol) was added to a stirred solution of 255B (3.49 g, 15.44 mmol) in 13 mL of THF at −78° C. dropwise. The mixture was stirred for an additional 4 h at 0° C. Ethylene oxide (1.05 mL) was added at −78° C. to the reaction solution. The mixture was warmed to rt and stirred overnight. Aqueous sat. NH4Cl was added and most of the THF was removed under reduced pressure. The mixture was extracted with ether (3×) and the combined organic layers were washed with water (1×) and brine (1×) and dried over Na2SO4. Purification by flash chromatography on silica gel eluting with 5% EtOAc/95% CH2Cl2 gave 2.8 g (10.4 mmol, 67%) of compound 255C as a yellow oil.

Provenance & Evidence