Water → methyl (E)-3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)benzoate

HRID 1690148ノート

反応式

HRID 1690148 の反応式
[CH2:1]([C:4]1[C:5](Cl)=[N:6][CH:7]=[C:8]([C:10]([O:19][CH2:20][O:21][CH3:22])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])[CH:9]=1)[CH:2]=[CH2:3].[H-].[Na+].[CH3:26][O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=1.O>CN(C)C=O>[F:12][C:11]([F:14])([F:13])[C:10]([C:8]1[CH:9]=[C:4](/[CH:1]=[CH:2]/[CH3:3])[C:5]([O:35][C:31]2[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=2)[C:28]([O:27][CH3:26])=[O:36])=[N:6][CH:7]=1)([O:19][CH2:20][O:21][CH3:22])[C:15]([F:18])([F:17])[F:16]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 88068Methyl 3-HydroxybenzoateHCID 592009063-Allyl-2-chloro-5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)pyridine

生成物 1

HCID 59201011methyl (E)-3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)benzoate収率 76.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-allyl-2-chloro-5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)pyridine (80 mg, 0.220 mmol) in N,N-dimethylformamide (2 mL), sodium hydride (14.4 mg, 0.330 mmol) and 3-hydroxybenzoic acid methyl ester (50 mg, 0.330 mmol) were added under ice-cold conditions, and the resultant mixture was stirred at 80° C. for 18 hours and further stirred at 100° C. for 3 hours. The reaction solution was added with water under room temperature and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and the title compound (81 mg, yield 76.5%) was obtained as a colorless oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

出典と根拠

ORDレコード
ord-bb683a28b36d48538b7fdb3fb2729e97
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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