tert-Butanol → HCID 22995909, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-trifluoromethanesulfonyloxy-8-vinylquinoline in 37 ml of tert-butanol and 37 ml of water is added to a suspension, cooled to 0° C. with an ice bath, of AD-mix-α in 300 ml of tert-butanol and 300 ml of water. The reaction mixture is stirred at 0° C. for 16 h and then sodium bisulfite with 300 ml of water is added. The mixture is stirred for 1 h at ambient temperature and extraction is carried out with ethyl acetate (3×200 ml). The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica chromatographic column (eluent: cyclohexane/ethyl acetate 1/1) to provide 12.0 g of 2-trifluoromethanesulfonyloxy-8-(1,2-dihydroxyethyl)quinoline in the form of a yellow oil. (Yield: 80%)

Provenance & Evidence