Water → HCID 10307943, compound

Participants

Reaction Steps

A mixture of 1-[6,7-dimethyl-5-(tetrahydro-pyran-2-yloxy)-benzofuran-2-yl]-ethanone (1.1 g) (prepared from 2,5-dihydroxy-3,4-dimethyl-benzaldehyde following the procedure of Steps 3, 4 and 5 of Example 13) and conc. HCl (10 drops) in MeOH (20 mL) was stirred at room temperature for 2 h. Water was poured into the mixture and left to precipitate overnight in the refrigerator. The precipitate was collected, washed with hexane and dried to give 1-(5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-ethanone as a light brown solid (490 mg). 1H NMR (CDCl3, 300 MHz) δ: 7.38 (s, 1H), 6.89 (s, 1H), 4.88 (1H, OH), 2.60, 2.50, 2.31 (3s, 9H) ppm. 13C NMR (CDCl3, 75 MHz) δ: 192.76, 155.45, 155.13, 153.72, 130.29, 127.27, 124.75, 117.44, 106.18, 29.30, 15.56, 15.28 ppm. MS (m/z): 205 (M+H+).

Provenance & Evidence