Methanol → HCID 57389078, compound

Participants

Reaction Steps

Compound O (21.9 g, 82.0 mmol) in H2O, THF, and MeOH (3:1:1, 255 mL) was treated with lithium hydroxide (9.80 g, 410 mmol) at 100° C. for 2 hours under N2. The reaction mixture was partially concentrated and the remaining aqueous phase was washed with dichloromethane (50 mL). The aqueous phase was acidified to pH 4-5 with 3 N HCl and then extracted with ethyl acetate (3×400 mL). The combined organic solutions were washed with saturated NaCl solution and dried over anhydrous Na2SO4. Filtration and concentration by rotary evaporation provided compound R (15.71 g, 98%) as an off-white powder. 1H NMR (CDCl3, 400 MHz) δ: 6.18 (d, 1H, J=2.0 Hz), 6.01 (d, 1H, J=2.0 Hz), 3.79 (s, 3H), 2.93 (q, 2H, J=7.0 Hz), 1.23 (t, 3H, J=7.5 Hz). ESMS m/z: 196.0 [M+H]+, 178.0 [M−OH]+.

Provenance & Evidence