m-Chloroperbenzoic acid → 3-Pyridinemethanol, 2-methyl-6-(trifluoromethyl)-, 1-oxide

HRID 271462노트

반응식

HRID 271462 반응식
[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([C:10]([F:13])([F:12])[F:11])[N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:19]>C(#N)C.CCOC(C)=O>[OH:9][CH2:8][C:7]1[C:2]([CH3:1])=[N+:3]([O-:19])[C:4]([C:10]([F:11])([F:13])[F:12])=[CH:5][CH:6]=1

참가 물질

5

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanol

생성물 1

HCID 598348163-Pyridinemethanol, 2-methyl-6-(trifluoromethyl)-, 1-oxide수율 25%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirring solution of (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (2.70 g, 14.1 mmol) in acetonitrile (20 mL) at room temperature was added dropwise a solution of 3-chloroperoxybenzoic acid (77% pure, 3.8 g, 16.9 mmol) in acetonitrile. The reaction mixture was stirred at room temperature for 16 h before concentration under reduced pressure. The residue was diluted with EtOAc, and the EtOAc solution was washed with 5% aqueous Na2S2O3, water, then saturated aqueous NaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (40 g) eluted with a gradient of EtOAc (30-100%) in hexanes to afford 730 mg (25%) of the title compound as a white solid. HPLC/MS: retention time=0.92 min, [M+H]+=208.0. In addition, (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (1.90 g) was recovered.

후처리

  1. washthe EtOAc solution was washed with 5% aqueous Na2S2O3, water
  2. dry with materialsaturated aqueous NaCl, dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified
  5. washeluted with a gradient of EtOAc (30-100%) in hexanes

출처 및 근거

ORD 기록
ord-bdc351eede304a2aa57de35d4f55a214
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

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