tert-Butanol → HCID 20714290, compound

Participants

Reaction Conditions

Reaction Steps

2.0 g of 2-ethyl-3-methyl-8-vinylquinoline, 65 ml of t-butanol and 65 ml of water are introduced into a 250 ml round-bottomed flask. The solution is cooled to 0° C. on an ice bath and 16.8 g of AD-mix-α (complex based on K2OsO2(OH)4, Fe(CN)6 and dihydroquinidine 1,4-phthalazinediyl diether as ligand) are added. Stirring is continued for 18 h at 0° C. and a solution of 12.6 g of sodium sulphite in 30 ml of water is added. The mixture obtained is stirred for 1 h at room temperature and is then extracted with ethyl acetate (2×200 ml). The organic phase is dried over magnesium sulphate and concentrated. The residue is purified by column chromatography on silica (elution solvent: 3/7 ethyl acetate/heptane). 2.0 g (yield: 86.5%) of (+)-2-ethyl-3-methyl-8-(1(S),2-dihydroxyethyl)quinoline are obtained in the form of a white solid.

Provenance & Evidence