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

HRID 1489391Notes

Reaction equation

HRID 1489391 reaction equation
[C:1]1([CH:7]([OH:10])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[CH3:16][O:17][N:18]=[C:19]([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1O.N(C(OCC)=O)=NC(OCC)=O>CCOCC>[CH3:16][O:17][N:18]=[C:19]([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:10][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 71471-Phenyl-1-propanolHCID 8028TetrahydrofuranHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1359761652-hydroxy-alpha-(1-imidazolyl)benzaldehyde O-methyloxime

Product 1

HCID 54515493alpha-(1-imidazolyl)-2-(1-phenylpropyloxy)benzaldehyde O-methyloxime

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thriphenylphosphine (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 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 to α-(1-imidazolyl)-2-(1-phenylpropyloxy)benzaldehyde O-methyloxime (0.63 g) as a colorless oil

Sources & evidence

ORD record
ord-ecf8380541f64e9a83a2148c5ae44417
Source dataset
uspto-grants-1997_10
Patent number
US05677465

Reaction notes

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