tert-Butanol → 3-(5,6-Dihydroxyhexyl)-1-methyluracil

Participants

Reaction Steps

A solution of 3-(5-hexenyl)-1-methyluracil (598 mg, 2.9 mmol), 4-methylmorpholine-N oxide (408 mg, 3.5 mmol), and a 2.5% solution in t-butanol of osmium tetroxide (3 drops) in acetone (15 mL) and water (5 mL) was stirred for 3 days. After addition of a saturated solution of sodium hydrosulfite (10 mL) and 15 minutes, the reaction mixture was added to water (15 mL) and extracted with 20% ethanol/dichloromethane (4×40 mL). The combined organic layers were dried over sodium sulfate and the solvent is evaporated under vacuum to give 461 mg (66%) 3-(5,6-dihydroxyhexyl)-1-methyluracil (inventive compound no. 1811) as a colorless oil.

Provenance & Evidence