Tetrahydrofuran → HCID 19895465, compound

Participants

Reaction Steps

To a solution of NaBH4 (0.2 g) in ethanol (10 ml) at ice bath temperature was added a solution of 3-cyano-2-nitrobenzaldehyde from Example 2c (0.93 g) in ethanol:tetrahydrofuran (15 ml:15 ml). After the addition was completed, the solution was warmed to ambient temperature and stirred for 30 minutes. The volatiles were removed under aspirator vacuum and the residue suspended in water. Dilute (1% aqueous) hydrochloric acid was added slowly until gas evolution had ceased. Ethyl acetate was then added followed by saturation of the aqueous layer with K2CO3. The layers were separated and the ethyl acetate layer was washed with brine, dried (Na2SO4) and concentrated to leave the title product (0.85 g, 90%) as a yellow solid: tlc, Rf =0.25, silica gel, ethyl acetate:hexane (1:1).

Provenance & Evidence