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

HRID 623421

反応式

HRID 623421 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-022f4767b1264c60b3aa5b35c2f153ea
出典データセット
uspto-grants-2016_04
特許番号
US09302991B2

関連ノート

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