N-tert-butylhydroxylamine → HCID 73096997, compound

HRID 1242266Notes

Reaction equation

HRID 1242266 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([NH:18][OH:19])([CH3:17])([CH3:16])[CH3:15]>CO>[C:14]([N+:18]([O-:19])=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 98586N-tert-butylhydroxylamineHCID 13046675HCID 13046675, compound

Product 1

HCID 73096997HCID 73096997, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-phenyl 1-hexanal (4.93 g, 28.0 mmol, 1 equiv) in methanol (50 ml) was added N-tert-butylhydroxylamine (3.00 g, 33.6 mmol, 1.2 equiv), and the mixture was stirred at rt. for 4 h. Concentration of the mixture gave a light colored oil which was purified by flash chromatography (EtOAc) to give N-tert-butyl-C-(5-phenylpentyl)nitrone (4.39 g, 89.0%) as a colorless oil: 1H NMR (CD3OD) δ 7.28–7.11 (m, 6H), 2.66–2.24 (m, 4H,), 1.72–1.24 (m, 15H).

Workup

  1. customConcentration of the mixture gave a light colored oil which
  2. customwas purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-36149463e5604098a31890c6eda2797a
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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