p-Toluenesulfonic acid → HCID 85100428, compound

HRID 1242267Notes

Reaction equation

HRID 1242267 reaction equation
[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1)[CH:3]=O.[C:15]([NH:19][OH:20])([CH3:18])([CH3:17])[CH3:16].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:15]([N+:19]([O-:20])=[CH:3][CH:2]([CH3:1])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 98586N-tert-butylhydroxylamineHCID 517827Cyclamen aldehyde

Product 1

HCID 85100428HCID 85100428, compoundYield 25.18%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of [2-methyl-3-(4-isopropylphenyl)-propionaldehyde] (3.0 g, 15.8 mmol, 1.0 equiv), N-tert-butylhydroxylamine (1.76 g, 19.7 mmol, 1.3 equiv) and toluene (60 ml) was added p-TsOH (50 mg), and the mixture was stirred at rt for 18 h. Removal of the solvent under reduced pressure gave a solid which was purified by column chromatography (EtOAc:hexane 1:1) to give N-tert-butyl-C-[2-(4-isopropylphenyl)-1-methyethyl]nitrone (1.04 g, 25.18%) as a white solid: 1H NMR (CDCl3) δ 7.12 (d, J=1.0, 4H), 6.63 (d, J=7.2 1H), 3.47–3.31 (m, 1H), 2.89–2.80 (m, 2H), 2.71–2.63 (dd, 1H), 1.44 (s, 9H), 1.25 (d, J=6.9, 3H).

Workup

  1. customRemoval of the solvent under reduced pressure
  2. customgave a solid which
  3. customwas purified by column chromatography (EtOAc:hexane 1:1)

Sources & evidence

ORD record
ord-2e17b65e597e45d2a313fade921944a1
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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