Dimethylformamide → HCID 15795689, compound

Participants

Reaction Steps

POCl3 (3.86 mL, 42.2 mmol) was added slowly to a stirring dimethylformamide (DMF) solution at 0° C. The mixture was cooled for 1 h before a DMF solution of 2-methyl azulene (2.0 g, 14.1 mmol) was added drop-wise. The reaction was mixed for 2 h at 0° C., and then quenched with cold 10% NaOH. The organic layer was extracted into ethyl acetate after which the extracts were washed with water and brine, dried with MgSO4 and purified using flash chromatography (ethyl acetate and hexane). The purified material was dried down into a dark red solid. Yield: 2.389 g, 89%. 1H NMR (400 MHz, CDCl3) δ 10.50 (s, 1H), 9.44 (d, J=9.73 Hz, 1H), 8.29 (d, J=9.72 Hz, 1H), 7.72 (t, J=9.82 Hz, 1H), 7.56 (t, J=9.82 Hz, 1H), 7.46 (t, J=9.67 Hz, 1H), 7.08 (s, 1H), 2.84 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 185.8, 154.9, 144.4, 142.1, 137.9, 136.4, 129.7, 128.5, 122.5, 120.3, 15.1. HRMS (ES) calcd. MH+(C12H11O) 171.0732 found 171.0804.

Provenance & Evidence