1,2-Dichloroethane → HCID 58762226, compound

HRID 1453017Notes

Reaction equation

HRID 1453017 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

5

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 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).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 1N HCl and EtOAc
  3. washThe organic layers were washed with saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe oil was purified by silica gel chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4e55e89794a94acca5fb11b000ef953d
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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