p-Anisoyl chloride → HCID 59736803, compound

Participants

Reaction Steps

To a solution of compound 150 (390 mg, 1.28 mmol) in pyridine was added 4-methoxybenzoyl chloride (181 mg, 1.06 mmol) and 4-(N,N-dimethylamino)pyridine (13 mg, 0.11 mmol). The mixture was stirred for 16 h and partitioned between EtOAc and H2O. The organic layer was washed with brine and some compound was collected by filtration. The filtrate was dried over MgSO4, filtered and concentrated in vacuo and then crystallized from a mixture of EtOAc/Hexanes. The two crops were combined affording the title compound 151 (358 mg, 72% yield). 1H NMR: (400 MHz, CD3OD) δ(ppm): 11.73 (s, 1H), 10.71 (s, 1H), 8.36 (d, J=2.0 Hz, 1H), 8.08 (d, J=8.6 Hz, 1H), 7.95 (d, J=9.0 Hz, 2H), 7.86 (d, J=0.8 Hz, 1H), 7.83 (dd, J=8.6, 2.0 Hz, 1H), 7.10 (d, J=9.0 Hz, 2H), 3.85 (s, 3H), 1.50 (s, 9H).

Provenance & Evidence