tert-Butanol → HCID 18918434, compound

Participants

Reaction Steps

31 (3.63 g, 16.7 mmol) is dissolved in 16 ml of a 1:1 mixture of water and acetone. After addition of N-methyl-morpholine-N-oxide (2.9 g, 24.8 mmol), a 1% solution of osmium tetroxide in tert. Butanol (7.23 ml, 0.28 mmol) is added. The mixture is stirred at room temperature for 20 h. Then 70 ml of a saturated sodium bisulfite solution is added. After 15 min stirring at room temperature, the reaction mixture is extracted with ethyl acetate. The organic layers are dried over sodium sulphate and evaporated. The crude product, 4.7 g of a yellow oil, is purified by Flash-chromatography (silica gel, ethyl acetate).

Provenance & Evidence