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

HRID 128912

反応式

HRID 128912 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4d2ce26ab71a473abd85b8cc9ab46a21
出典データセット
uspto-grants-1995_11
特許番号
US05466661

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