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Sodium hydride → isopropyl-4-[(E)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate

HRID 1371024
ノート
印刷プレビュー

反応式

HRID 1371024 の反応式
[CH:1]([O:4][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[O:14])=[CH:8][CH:7]=1)([CH3:3])[CH3:2].[H-].[Na+].[CH2:25](Br)[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])(=O)C.[NH4+]>CN(C=O)C>[CH:1]([O:4][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:13](=[O:14])[C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH2:25]/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:8][CH:7]=1)([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 517165Ammonium AcetateHCID 18510263Isopropyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate

生成物 1

HCID 18510243isopropyl-4-[(E)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate収率 29.2%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

To a solution of isopropyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate(0.970 g, 3.23 mmol) in DMF (10 ml) at 0° C. was added NaH (0.100 g, 4.16 mmol). After a period of 0.5 h to the reaction mixture was added a solution of cinnamyl bromide (0.630 g, 3.21 mmol) in DMF (10 ml), and the reaction was stirred at room temperature for 1 hour. Saturated ammonium acetate solution (20 ml) was added and the mixture was extracted with ethyl acetate (20 ml). The organic phase was washed with brine and dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography using a gradient from hexane/ethyl acetate 2% to hexanel ethyl acetate 10% giving 0.39 g of the title compound.

後処理

  1. extractionthe mixture was extracted with ethyl acetate (20 ml)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-b553de4fae04436881e623acce1a870f
出典データセット
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06583126B2

反応ノート

読み込み中…

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