Toluene → 2-[3-Methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinaldehyde

HRID 1294168

반응식

HRID 1294168 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26])[CH2:6][O:7][C:8]1[N:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#N.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=[O:54])C>CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:24][C:25]=1[CH3:26])[CH2:6][O:7][C:8]1[N:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:54]

참가 물질

7

반응물 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 688835522-[3-Methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinonitrile

생성물 1

HCID 865915632-[3-Methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinaldehyde

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

To a mixture of 2-[3-methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinonitrile (4.25 g) and toluene (150 mL) was dropwise added a solution (0.95 M, 23.0 mL) of diisobutylaluminum hydride in hexane at −78° C. After stirring for 1 hr the reaction mixture was warmed to room temperature and the mixture was further stirred for 1 hr. A saturated aqueous ammonium chloride solution (35 mL) was dropwise added to the mixture and the mixture was stirred at room temperature for 30 min. To the mixture was added ethyl acetate and the insoluble materials were filtered off. The filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give 2-[3-methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinaldehyde as crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless crystals (710 mg, 17%). melting point: 99-100° C.

후처리

  1. stirringthe mixture was further stirred for 1 hr
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. filtrationthe insoluble materials were filtered off
  4. washThe filtrate was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9a72ee0362144bfea8fde62492237a52
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238716B2

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