Dichloromethane → HCID 86631902, compound

Participants

Reaction Conditions

Reaction Steps

To a flame-dried 50 mL flask was added methyl(S)-2-hydroxy-3-methylbutyrate (330 mg, 2.5 mmol), anhydrous CH2Cl2 (1.5 mL), cyclohexane (3 mL). The reaction flask was cooled to 0° C., and benzyl 2,2,2-trichloroacetimidate (0.464 mL, 2.5 mmol) was added with stirring. To the resulting solution was added trifluoromethanesulfonic acid (0.044 mL, 0.5 mmol). After addition was completed, the reaction was warmed to room temperature and was stirred for 17 hrs. The reaction was monitored by 1H NMR, and most of SM was consumed. The reaction mixture was filtered, and collected solid was rinsed with cyclohexane (2×10 mL). The filtrate was washed with saturated NaHCO3 (5 mL), water (2×5 ml), brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude oil was purified by flash chromatography eluting with EtOAc-Hexanes (0.5:99.5) to afford the desired compound methyl (S)-methyl-2-benzyloxy-3-methylbutanoate (319 mg, 1.44 mmol, 57% yield). 1H NMR (300 MHz, CDCl3): consistent with proposed structure.

Provenance & Evidence