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

HRID 128912

반응식

HRID 128912 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d2ce26ab71a473abd85b8cc9ab46a21
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466661

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