1,2-Dichloroethane → HCID 58762226, compound

Reaction equation

Cl.[CH3:2][NH:3][O:4][CH3:5].C(Cl)CCl.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([OH:29])=O)=[CH:21][CH:20]=1>>[CH3:5][O:4][N:3]([CH3:2])[C:27](=[O:29])[CH2:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 8471Triethylamine

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

HCID 957503-(p-Methoxyphenyl)propionic acid

Product 1

HCID 58762226HCID 58762226, compoundYield 85.5%

Procedure

N,O-dimethylhydroxylamine hydrochloride (5.41 g, 55.5 mmol), EDC (12.77 g, 66.6 mmol), followed by triethylamine (17 mL, 122 mmol) were added to a cooled 0° C. solution of 3-(4-methoxyphenyl)propionic acid (10 g, 55.5 mmol). The reaction mixture was stirred for 15 h under N2 and then concentrated. The residue was partitioned between 1N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to an oil. The oil was purified by silica gel chromatography (40% EtOAc in hexanes) to give a clear oil (10.6 g, 85%). 1H NMR (CDCl3): δ 2.70 (t, 2H, J=7.5 Hz), 2.91 (t, 2H, J=7.5 Hz), 3.18 (s, 3H), 3.61 (s, 3H), 3.79 (s, 3H), 6.83 (d, 2H, J=8.7 Hz), 7.15 (d, 2H, J=8.7 Hz).