Nitrosobenzene → HCID 59294637, compound

HRID 1099334Notes

Reaction equation

HRID 1099334 reaction equation
C1CCN2C(=NCCC2)CC1.[CH:12]1([CH:18]=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[N:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>ClCCl>[OH:21][N:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:19]

Participants

5

Reactant 3

HCID 11473NitrosobenzeneHCID 16275CyclohexanecarboxaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 59294637HCID 59294637, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (15 mg, 0.1 mmol) was added under argon to a solution of cyclohexanal (112 mg, 1 mmol), nitrosobenzene (107 mg, 1 mmol) and catalyst (36.4 mg, 0.1 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 10 min. The solvent was removed under vacuum, and the residue was purified by flash silica gel column chromatography using hexane and ethyl acetate as the eluents.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-44988dbc2c47453691d74ffd04f45483
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Reaction notes

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