Benzo[1,5-b']dithiophene-4,8-dione, 2-(1-hydroxyethyl)- → HCID 388026, compound

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Reaction Steps

Compound 13 was reduced with NaBH4 as in the preparation of 10. Column chromatography on silica gel eluting with CHCl3:MeOH (100:1) gave 14 as a yellow solid (mp 218-219° C.) in a 90% yield. IR (KBr) 1650, 1670 (C═O), 3100-3500 (OH) cm−1; 1H NMR (DMSO-d6) δ 1.36 (d, J=6.0 Hz, 3H, C-7-CH3), 1.48 (d, J=6.0 Hz, 3H, C-2-CH3), 5.05 (s, 1H, C-2-OH), 5.33 (s, 1H, C-7-OH), 5.52 (m, 1H, C-7-CH), 6.17 (m, 1H, C-2-CH), 7.41 (s, 1H, H-3), 7.97 (s, 1H, H-6); 13C NMR (DMSO-d6) δ 24.8 (C-7-CH3), 25.5 (C-2-CH3), 64.1 (C-7-CH), 64.9 (C-2-CH), 120.7 (C-3), 130.1 (C-6), 174.7 (C-4), 175.3 (C-8); MS m/z 308 (M+); Anal. (C14H12O4S2) C, H.

Provenance & Evidence