1,2-Dichloroethane → HCID 58762226, compound

HRID 858570Notes

Reaction equation

HRID 858570 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 1 N 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%).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 1 N 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-ae51d258e3424a28a3f351c218b701b6
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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