HCID 388023, compound → Benzo[1,5-b']dithiophene-4,8-dione, 2-(1-hydroxyethyl)-

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Reaction Steps

To a suspension of 9 (3.0 g, 11.2 mmol) in MeOH (200 mL) was added NaBH4 (1.5 g, 39.7 mmol) and stirring continued for 2 h. After acidification with dilute HCl, the solution was extracted with CHCl3. The organic fraction was washed with water, dried, and condensed. The residue was purified by column chromatography (silica gel, CHCl3) to give 10 as a yellow solid (mp 166-168° C.) in a 93% yield. IR (KBr) 1650, 1680 (C═O), 3200-3600 (OH) cm−1; 1H NMR (DMSO-d6) δ 1.48 (d, J=6.3 Hz, 3H, CH3), 5.02-5.07 (m, 1H, CH), 6.10 (d, J=4.8 Hz, 1H, OH), 7.45 (s, 1H, H-3), 7.62 (d, J=5.1 Hz, 1H, H-7), 8.15 (d, J=5.1 Hz, 1H, H-6); 13C NMR (DMSO-d6): δ 25.3 (C-2-CH3), 64.6 (C-2-CH), 120.7 (C-3), 126.1 (C-7), 135.5 (C-6), 163.0 (C-2), 174.0, 174.4 (C-4, C-8); MS m/z 264 (M+); Anal. (Cl2H8O3S C, H.

Provenance & Evidence