O-Benzylhydroxylamine → HCID 85993143, compound

HRID 271971Notes

Reaction equation

HRID 271971 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4](=[CH2:13])[CH:5](OC(=O)C)[CH2:6][CH2:7][CH3:8].[CH2:15]([O:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]([CH2:13][NH:23][O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 102313O-BenzylhydroxylamineHCID 103304023-acetoxy-2-methylenehexanoic acid methyl ester

Product 1

HCID 85993143HCID 85993143, compoundYield 212.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-acetoxy-2-methylenehexanoic acid methyl ester (4.00 g, 20 mmol) and O-benzylhydroxylamine (7.39 g, 60 mmol) in THF (30 mL) is allowed to react at RT under N2 for 2 days. The reaction mixture is concentrated on Rotavap under reduced pressure (20 mbar) until no further solvent distills. The residue liquid is dissolved in ethyl acetate (75 mL) and washed with saturated aqueous sodium bicarbonate solution (50 mL). The ethyl acetate layer is concentrated on Rotavap under reduced pressure (20 mbar) until no further solvent distills to afford a colorless liquid (11.2 g).

Workup

  1. customto react at RT under N2 for 2 days
  2. concentrationThe reaction mixture is concentrated on Rotavap under reduced pressure (20 mbar) until no further solvent
  3. distillationdistills
  4. dissolutionThe residue liquid is dissolved in ethyl acetate (75 mL)
  5. washwashed with saturated aqueous sodium bicarbonate solution (50 mL)
  6. concentrationThe ethyl acetate layer is concentrated on Rotavap under reduced pressure (20 mbar) until no further solvent
  7. distillationdistills

Sources & evidence

ORD record
ord-c34d99016fea4b629a649f1050634fe2
Source dataset
uspto-grants-2008_11
Patent number
US07452999B2

Reaction notes

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