Formaldehyde → HCID 53312154, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (2.03 g, 46.3 mmol) in 40 mL of anhydrous toluene is cooled to 0° C. by ice bath, add a solution of (S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-pyrrolidin-2-one (4a, R1=1-butenyl, R4=phenyl) (14.7 g, 35.7 mmol) in anhydrous toluene dropwise, stir for 30 min, then add paraformaldehyde (2.2 g, 71.4 mmol) in portions, heat to reflux under nitrogen atmosphere for 4 h, cool to room temperature, quench with saturated NH4Cl aqueous solution, extract with toluene, the combined organic extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4 and concentrate to obtain (R)-5-Biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-3-methylene-pyrrolidin-2-one (1a, R1=1-butenyl). 1HNMR (400 MHz, CDCl3): 1.07 (t, 3H, CH3H), 2.12 (m, 2H, CH2H), 2.57 (m, 2H, 3-CH2), 2.65 (m, 1H, 5-CH2), 3.16 (m, 1H, 5-CH2), 4.14 (m, 1H, 4-CH), 5.22 (s, 1H, C═CHH), 5.27 (m, 1H, CH═CH), 5.91 (d, 1H, HC═CHH), 6.85 (d, 1H, HC═CH—N), 7.14˜7.51 (9H, m, aromatic).

Provenance & Evidence