Ethylvanillin → HCID 68633378, compound

Participants

Reaction Steps

NaB(OAc)3H (8 g, 0.038 mol) was added in portions for 30 min to a mixture of pyrrolidine (3.1 mL, 0.038 mol) and 3-ethoxy-4-hydroxybenzaldehyde (5 g, 0.03 mol) in CH2Cl2 (50 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon Ar. The mixture was stirred for 12 h and cooled with an ice bath. 10N NaOH (3.8 mL) and water (30 mL) were added. The organic layer was separated. The aqueous one was extracted with chloroform (2×100 mL). The extracts were evaporated. The residue was purified by chromatography (silica gel 40-63μ, 100 g, CCl4—CHCl3, CHCl3/MeOH 100:0→90:10) to give the title compound (4.8 g, 73%) was obtained as dark-yellow crystals. 1H NMR data (DMSO-d6): 8.65 (s, 1H ArOH), 6.81 (d, 1H, J=1.71, Ar—H), 6.70 (d, 1H, J=7.8, Ar—H); 6.65 (dd, 1H, J1=7.8, J2=1.7, Ar—H), 3.98 (q, 2H, CH2CH3), 3.42 (s, 2H, ArCH2), 2.33-2.45 (m, 4H, pyrrolidine (CH2)2N), 1.59-1.73 (m, 4H, CH2CH2CH2CH2); 1.31 (t, 3H, J=6.9, CH2CH3).

Provenance & Evidence