Methanol → HCID 69082735, compound

Participants

Reaction Steps

A solution of 108 (300 mg, 0.7 mmol) in dichloromethane (20 mL) was treated with BCl3 (7 mL, 7 mmol, 1 M in dichloromethane) for 2 hours at −60° C., then quenched by the addition of methanol (10 mL). Volatiles were distilled out under vacuum to give a residue, which was dissolved into methanol (5 mL) and neutralized by Con. NH4OH (2 ml, 26% aqueous solution). After concentration, the crude product was purified by a silica gel column, eluted with 10% methanol in dichloromethane to give the title compound as a white solid (35 mg, 20%); (ES, m/z) [M+H]+ 265.0; 1HNMR (300 MHz, D2O) δ 6.16 (d, J=6.3 Hz, 1H), 4.60 (t, J=4.8 Hz, 1H), 4.45 (t, J=4.8 Hz, 1H), 4.10 (t, J=6.0 Hz, 1H), 3.92 (t, J=4.8 Hz, 1H), 3.62-3.66 (m, 1H), 3.42-3.60 (m, 1H), 2.90 (s, 6H), 2.06-2.20 (m, 1H), 1.67-1.88 (m, 1H).

Provenance & Evidence