Sodium borohydride → 1504-63-8

Participants

Reaction Steps

(E)-4-Nitrocinnamaldehyde (3,1.0 g, 5.65 mmol) was dissolved in methanol (70 ml ) in a 100 ml flask. Sodium borohydride (106 mg, 2.8 mmol) was added portionwise while stirring. Stirring was continued for 0.5 hr. The solution was evaporated to dryness. The residue was dissolved in a chloroform/water mixture and the organic phase was separated. It was washed twice with distilled water and dried over anhydrous MgSO4. Evaporation of solvent and crystallization from CH2Cl2-hexanes yielded compound 4 (1.0 g, 98%) as a pale yellow solid: mp 129-130° C.; Rf=0.77 (10%CH3OH—CH2Cl2); 1H NMR (300 MHz, CDCl3): δ8.20 (d, aromatic, 2H, J=8.0 Hz), 7.53) (d, aromatic, 2H, J=8.0 Hz), 6.73) (d, 1H, J=16 Hz), 6.57 (m, 1H), 4.20 (d, 2H, J=5.2 Hz), 1.56 (s, 1H); 13C NMR (CDCl3): δ147.16(C), 143.48(C), 133.81(CH), 128.46(CH), 127.13(CH), 124.23(CH), 63.30(CH2).

Provenance & Evidence