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

HRID 1371015
ノート
印刷プレビュー

反応式

HRID 1371015 の反応式
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1.[H-].[Na+].[CH2:23](Br)[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])(=O)C.[NH4+]>CN(C=O)C>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:20])=[CH:9][CH:8]=2)[CH2:23]/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:12])=[CH:18][CH:17]=1
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 18510220Methyl 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate

生成物 1

HCID 18510204methyl 4-[(E)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate収率 62.9%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

To methyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate(0.48 g, 1.76 mmol) in DMF (5 ml) at 0° C. was added NaH (0.05 g), 2.08 mmol). After a period of 0.5 h, a solution of cinnamyl bromide (0.35 g) in DMF (5 ml) was added to the reaction mixture. The reaction mixture was stirred at r.t. for 1 hour. Ammonium acetate saturated 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 and evaporated to dryness. The residue was purified by flash chromatography using hexane/ethyl acetate 30% to give 0.43 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. customevaporated to dryness
  5. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-1cf1461a892a4504b872cdb623b381e1
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

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