Hydrochloric Acid → 1-(6-(Difluoromethoxy)pyridin-3-yl)ethanone

HRID 1690177노트

반응식

HRID 1690177 반응식
CON(C)C(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:11][CH:12]([F:14])[F:13].[CH3:17][Mg]Br.Cl.[C:21](=[O:24])([O-])O.[Na+]>O1CCCC1>[F:14][CH:12]([F:13])[O:11][C:6]1[CH:5]=[CH:10][C:9]([C:21](=[O:24])[CH3:17])=[CH:8][N:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86639409N-methoxy-N-methyl-2-difluoromethoxynicotinamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 669048941-(6-(Difluoromethoxy)pyridin-3-yl)ethanone수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-methoxy-N-methyl-2-difluoromethoxynicotinamide (336 mg, 1.45 mmol) was dissolved in tetrahydrofuran (7.3 mL). 0.93 M methylmagnesium bromide (2.4 mL, 2.18 mmol) was added dripwise at 0° C. under an argon atmosphere. The resultant mixture was stirred for 10 minutes and added with 1N hydrochloric acid at the same temperature. Subsequently, the reaction solution was added with a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified using silica-gel column chromatography (n-hexane/ethyl acetate=4/1). 1-(2-(Difluoromethoxy)pyridin-5-yl)ethanone (264 mg, yield 98%) was obtained as a yellow oil.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified

출처 및 근거

ORD 기록
ord-425253f52f42453287381bed101c7997
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153634B2

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