Formaldehyde → HCID 53312154, compound

Participants

Reaction Steps

(S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (4a, R1=styryl, R4=phenyl) (0.50 g, 1.1 mmol) is dissolved in 2 mL of anhydrous toluene, add sodium hydride (65 mg, 1.5 mmol) in portions then paraformaldehyde (66 mg, 2.2 mmol) in one portion, the result mixture is heat to reflux for 4 h under nitrogen atmosphere. The reaction mixture is cooled to room temperature, then quench with saturated NH4Cl aqueous solution, extract with toluene, the organic extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4, evaporate the solvent under vacuum to obtain (R)-5-biphenyl-4-ylmethyl-3-methylene-1-((E)-styryl)-pyrrolidin-2-one (1a, R1=styryl) which could be used in next step directly. 1HNMR (400 MHz, CDCl3): 2.68 (m, 2H, 3-CHH+5-CH2H), 2.81 (m, 1H, 3-CHH), 3.28 (m, 1H, 5-CH2H), 4.32 (m, 1H, 4-CH), 5.35 (s, 1H, C═CHH), 6.04 (s, 1H, C═CHH), 6.23 (d, 1H, C═CHH), 7.21˜7.72 (m, 15H, aromatic+C═CHH).

Provenance & Evidence