3-Phenylbutanal → N-tert-butyl-C-(2-phenylpropyl)nitrone

HRID 1242268Notes

Reaction equation

HRID 1242268 reaction equation
[C:1]1([CH:7]([CH3:11])[CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([NH:16][OH:17])([CH3:15])([CH3:14])[CH3:13]>C1C=CC=CC=1>[C:12]([N+:16]([O-:17])=[CH:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:11])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 859793-PhenylbutanalHCID 98586N-tert-butylhydroxylamine

Product 1

HCID 86593654N-tert-butyl-C-(2-phenylpropyl)nitroneYield 92.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 3-phenylbutyraldehyde (10.0 g, 67.5 mmol, 1.0 equiv) and benzene (150 ml) and silica gel (5 g) was added N-tert-butylhydroxylamine (7.22 g, 81.0 mmol, 1.2 equiv) and the mixture stirred at rt for 18 h. The mixture was filtered and the filtrate was concentrated under vacuum to give N-tert-butyl-C-(2-phenylpropyl)nitrone (13.74 g, 92.80%) as a light yellow oil. 1H NMR (CDCl3) δ 7.33–7.19 (m, 5H), 6.65 (t, 1H), 3.18–3.04 (m, 1H), 2.90–2.65 (m, 2H), 1.40 (s, 9H), 1.34–1.32 (d, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-10ffcbf8f3974b93b3185070f09ec56f
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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