1-Phenyl-1-propanol → alpha-(1-imidazolyl)-2-(1-phenylpropyloxy)benzaldehyde O-methyloxime

HRID 128912

Reaction equation

HRID 128912 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([CH:26]([OH:29])[CH2:27][CH3:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:30][O:31][N:32]=[C:33]([N:41]1[CH:45]=[CH:44][N:43]=[CH:42]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1O.N(C(OCC)=O)=NC(OCC)=O>CCOCC.C1COCC1>[CH3:30][O:31][N:32]=[C:33]([N:41]1[CH:45]=[CH:44][N:43]=[CH:42]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:29][CH:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 71471-Phenyl-1-propanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1359761652-hydroxy-alpha-(1-imidazolyl)benzaldehyde O-methyloxime

Product 1

HCID 54515493alpha-(1-imidazolyl)-2-(1-phenylpropyloxy)benzaldehyde O-methyloximeYield 94.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (1.05 g), 1-phenylpropyl alcohol (0.54 g) and THF (20 ml) were added to 2-hydroxy-α-(1-imidazolyl)benzaldehyde O-methyloxime (0.43 g), and diethyl azodicarboxylate (0.70 g) was added under ice-cooling over 10 minutes. Then the mixture was stirred at room temperature for 2 hours. After completion of the reaction, ether (100 ml) was added, the mixture was washed with water (80 ml) twice, and the ether layer was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to give α-(1-imidazolyl)-2-(1-phenylpropyloxy)benzaldehyde O-methyloxime (0.63 g) as a colorless oil.

Workup

  1. additionwas added under ice-
  2. temperaturecooling over 10 minutes
  3. additionwas added
  4. washthe mixture was washed with water (80 ml) twice
  5. concentrationthe ether layer was concentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4d2ce26ab71a473abd85b8cc9ab46a21
Source dataset
uspto-grants-1995_11
Patent number
US05466661

Linked notes

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