Phenol → HCID 131733439, compound

Participants

Reaction Conditions

Reaction Steps

Phenol (7, Intermediate I) (0.50 g, 1.87 mmol) and K2CO3 (1.29 g, 9.35 mmol) were added to a solution of (6-methylpyridin-2-yl)methyl methanesulfonate (412 mg, 2.05 mmol) in DMF (20 mL) and the reaction mixture was heated under reflux at 90° C. for 18 h. The reaction mixture was diluted with EtOAc and washed with water and brine. Drying over anhydrous Na2SO4 and concentration under reduced pressure gave (R)-tert-butyl (3-hydroxy-3-(3-((6-methylpyridin-2-yl)methoxy)phenyl)propyl)carbamate as pale yellow liquid. Yield (200 mg, 72%); 1H NMR (400 MHz, CDCl3); δ 7.59 (t, J=8.0 Hz, 1H), 7.32 (d, J=7.2 Hz, 1H), 7.23 (s, 1H), 7.07 (d, J=8.0 Hz, 1H), 7.03 (s, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.87 (dd, J=8.0, 2.4 Hz, 1H), 5.17 (s, 2H), 4.86 (bs, 1H), 4.71 (bs, 1H), 3.49-3.48 (m, 1H), 3.19-3.11 (m, 2H), 2.57 (s, 3H), 1.88-1.82 (m, 2H), 1.45 (s, 9H); MS: m/z 373.20 [M+H]+.

Provenance & Evidence