Sodium Hydroxide → HCID 18368053, compound

Participants

Reaction Steps

To a solution of 3-acetylamino-6-chloro-1-ethoxycarbonyl-2-(3-acetoxymethyl-2-furoyl) indole (step 3, 180 mg, 0.4 mmol) in a mixture of ethanol (10 ml) and water (5 ml) was added 2N aqueous sodium hydroxide (2 ml) at room temperture. After stirring for 1.5 h, the mixture was poured into saturated aqueous ammonium chloride (50 ml) and extracted with ethyl acetate (100 ml). The organic layer was washed with brine (50 ml), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1/1), and the product recrystalized from acetone/hexane to give 98 mg (73%) of the titled compound as a yellow crystalline solid. m.p.: 196-198° C. 1H-NMR (CDCl3) δ: 10.6 (1H, br s), 9.52 (1H, br s), 8.33 (1H, d, J=9.2 Hz), 7.66 (1H, br s), 7.30 (1H,br s), 7.01 (1H, d, J=9.2 Hz), 6.66 (1H, br s), 4.81 (2H, s), 2.32 (3H, s). The signal due to H of OH was not observed.

Provenance & Evidence