Benzaldehyde, 4-(phenylmethoxy)- → alpha-(4Benzyloxyphenyl)-N-cyclopentylnitrone

HRID 2305805Notes

Reaction equation

HRID 2305805 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1([NH:22][OH:23])[CH2:21][CH2:20][CH2:19][CH2:18]1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[N+:22]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[O-:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 10219393N-cyclopentylhydroxylamine

Product 1

HCID 74008259alpha-(4Benzyloxyphenyl)-N-cyclopentylnitroneYield 85.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-benzyloxybenzaldehyde (20 g, 94.23 mmol), N-cyclopentylhydroxylamine (14.3 g, 141.34 mmol), molecular sieves (60 g, 4A) and silica gel (15 g) in chloroform (300 mL) was stirred at room temperature under argon atmosphere for 48 hrs and then was refluxed for an additional 3 hrs. The mixture was filtered and rotary evaporated to give crystals which were recrystallized from hexanes and EtOAc to provide the title compound as white crystals, 23.7 g, 85.1% yield), m.p. 115.1° C. (Rf=0.35 on a silica gel plate using hexanes:EtOAc, 1:1, v:v, as an eluant).

Workup

  1. temperaturewas refluxed for an additional 3 hrs
  2. filtrationThe mixture was filtered
  3. customrotary evaporated
  4. customto give crystals which
  5. customwere recrystallized from hexanes and EtOAc

Sources & evidence

ORD record
ord-b099b38d73e44c0c8fc3322dce91190c
Source dataset
uspto-grants-2002_08
Patent number
US06441032B1

Reaction notes

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