tert-Butanol → HCID 13755108, compound

Participants

Reaction Steps

[DHQD]2PHAL (54.5 mg, 0.25 mol %), methyl (E)-3-(4-methoxyphenyl)-2-propenoate (5.38 g, 28 mmol), N-methyl morpholine N-oxide (60% aqueous solution, 7.0 ml) and tert-butanol (11.2 ml) were charged to a 100 ml 3-neck flask and stirred at room temperature. Potassium osmate (VI) dihydrate (21.4 mg, 0.2 mol %) was added portionwise and the reaction was stirred at room temperature. The reaction procedure was monitored by HPLC. After 17 hours, Tiron (200 mg) was added to quench the reaction, followed by water (50 ml). The mixture was allowed to stir for one hour, ethyl acetate (50 ml) was added to the mixture and the resultant two layers were vigorously stirred for 30 minutes. The organic phase was removed and washed with water, dried (Na2SO4) and evaporated to dryness on a rotary evaporator. The product was purified by flash column chromatography using DCM: ethyl acetate (3:2) as eluant. Evaporation of the appropriate fractions gave methyl 2,3-dihydroxy-3- (4-methoxyphenyl)propanoate as a white crystalline solid (3.2 g, 62%). mp. 108° C., [α]D=−1.2° (THF, conc.=0.01306 22° C.). 1H-NMR was in accordance with expected signals.

Provenance & Evidence