Sodium Bicarbonate → Ethanone, 1-[6-(2,2,2-trifluoroethoxy)-3-pyridinyl]-

HRID 623421

반응식

HRID 623421 반응식
CON(C)[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:7][CH:6]=1.[CH3:19][Mg]Br.C(=O)([O-])O.[Na+]>O1CCCC1>[F:16][C:13]([F:14])([F:15])[CH2:12][O:11][C:8]1[N:7]=[CH:6][C:5]([C:4](=[O:17])[CH3:19])=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 86707284N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 58629124Ethanone, 1-[6-(2,2,2-trifluoroethoxy)-3-pyridinyl]-수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy)nicotinamide (6.54 g, 24.8 mmol, Step-2) in tetrahydrofuran (80 mL) is added dropwise 1.06M methylmagnesium bromide (46.7 mL, 49.5 mmol) at 0° C. The reaction mixture is stirred at room temperature for 1.5 hours. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate (100 mL) and extracted with ethyl acetate (300 mL). The organic layer is washed with water (100 mL×2) and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1) to give 4.51 g (83% yield) of the title compound as colorless oil.

후처리

  1. extractionextracted with ethyl acetate (300 mL)
  2. washThe organic layer is washed with water (100 mL×2)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-022f4767b1264c60b3aa5b35c2f153ea
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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