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

HRID 1690177ノート

反応式

HRID 1690177 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86639409N-methoxy-N-methyl-2-difluoromethoxynicotinamideHCID 178418573HCID 178418573、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-425253f52f42453287381bed101c7997
出典データセット
uspto-grants-2012_04
特許番号
US08153634B2

反応ノート

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