Methanol → HCID 14971865, compound

Participants

Reaction Conditions

Reaction Steps

5-(3-Methoxyphenyl)-4-oxazolecarboxamide (1.29 g, 5.9 mmol) was dissolved in dichloromethane (120 mL) and cooled to about 0° C. under N2. Boron tribromide solution (29 mL of 1 M in dichloromethane) was added dropwise and the solution stirred about 18 hours at room temperature. Methanol (10 mL) was added dropwise {caution: reacts vigorously}, and after being stirred 10 min the solution was concentrated onto SiO2 and chromatographed (elution with 20% methanol/ethyl acetate) to give the phenol 848 mg (70%), mp 202°-204° C.IR (KBr, cm-1) 3398, 3188, 3132, 1684, 1608, 1572, 1254, 1190, 866, 694, 618. 1H NMR (300 MHz, DMSO-d6)δ 6.82 to 6.85 (1H, m), 7.26 (1H, t, J=8.0 Hz) 7.56 to 7.69 (4H, m), 8.49 (1H, s), 9.66 (1H, s). 13C NMR 75 MHz, DMSO-d6) ppm 114.62, 116.95, 118.59, 128.08, 129.04, 129.52, 149.87, 151.10, 157.22, 162.80. m/e 205 (MH+).

Provenance & Evidence