Sodium Hydroxide → HCID 117729163, compound

Participants

Reaction Steps

To a stirred mixture of Intermediate 23a (0.774 g, 4.27 mmol) in ethyl acetate (4 mL) and 1 M aqueous NaOH (7.7 mL, 7.7 mmol) was added 2,2,2-trichloroethyl chloroformate (0.62 mL, 4.50 mmol) and the mixture was stirred at room temperature for 1.5 h. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with water and saturated aqueous NaCl, then evaporated to give the title compound (1.57 g) as an oil. LCMS (Method 3): Rt 4.28 min, m/z 356/358/360 [MH+]. 1H NMR (300 MHz, CDCl3): 0.90 (3H, t, J 7.5 Hz), 1.28 (9H, s), 1.78-1.87 (2H, m), 3.92 (2H, t, J 7.4 Hz), 4.83 (2H, s), 6.08 (1H, s), 6.46 (1H, s).

Provenance & Evidence