Toluene → 2-Pyridinemethanol, 5-(difluoromethoxy)-

HRID 15046

반응식

HRID 15046 반응식
C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.C([O:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH:30]([F:32])[F:31])=[CH:25][N:24]=1)=O)C.[BH4-].[Na+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CO.C1COCC1>[F:32][CH:30]([F:31])[O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:21][OH:20])=[N:24][CH:25]=1

참가 물질

8

반응물 5

HCID 1140TolueneHCID 62649Sodium sulfate decahydrateHCID 4311764Sodium borohydrideHCID 21225700DiisobutylaluminumhydrideHCID 68430338Ethyl 5-(difluoromethoxy)picolinate

생성물 1

HCID 684317562-Pyridinemethanol, 5-(difluoromethoxy)-수율 87%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A toluene solution (13.8 mL, 13.8 mmols) of 1N diisobutylaluminium hydride was added to a THF solution (40 mL) of 2-ethoxycarbonyl-5-difluoromethoxypyridine (1.0 g, 4.6 mols) and stirred at 0° C. for 40 minutes. Successively sodium borohydride (174 mg, 4.6 mmols) and methanol (2 mL) were added and stirred at 0° C. for 30 minutes. Sodium sulfate decahydrate was added to the reaction liquid and stirred overnight at room temperature. Filtering the insoluble matter with Celite, the solvent was concentrated under reduced pressure. The residue was purified on silica gel column chromatography (C-300, hexane:ethyl acetate=3:2-2:3) to provide the title compound (738 mg, 87%).

후처리

  1. stirringstirred at 0° C. for 30 minutes
  2. stirringstirred overnight at room temperature
  3. filtrationFiltering the insoluble matter with Celite
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe residue was purified on silica gel column chromatography (C-300, hexane:ethyl acetate=3:2-2:3)

출처 및 근거

ORD 기록
ord-2b2063a5771f49eaa882928ed87a2712
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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