Acetic Acid → HCID 21449232, compound

Participants

Reaction Steps

4-Methoxy-6,11-dihydroxy-7,8-dihydro-5,9 (10H),12-naphthacenetrione (IV) (45.3 mg, 0.134 mmole) and KCN (300 mg) were placed in 50% CHCl3 /EtOH (8 ml) and cooled to 0°. HOAc (0.4 ml) was added and the mixture was stirred at 23° for 5 hr. The reaction mixture was diluted with H2O (15 ml), the organic phase separated and the aqueous phase extracted with CHCl3 (10 ml). The organic solutions were combined, dried over Na2SO4 and evaporated. The residue was chromatographed (8 g silica gel, 98.2 CHCl3 /MeOH) to afford 38.0 mg (77%) of (V): mp 232°-235° (dec); irnujol 2.93 (OH), 6.20, 6.31 μ (chelated quinone); pmr 100 MHz CDCl3 δ 2.1-2.4 (m, 2H, 8-H2), 2.8-3.4 (m, 5H, benzylic H's and 9-OH), 4.08 (s, 3H, OMe), 7.36 (dd, 1H, J = 8Hz and J = 1Hz, 3-H), 7.74 (t, 1H, J = 8Hz, 2-H), 7.99 (dd, 1H, J = 8Hz and J = 1Hz, 1-H), 13.28 (s, 1H, phenolic OH), 13.68 (s, 1H, phenolic OH); ms 12 ev m/e (%) 338 M-HCN (100).

Provenance & Evidence