Sodium hydride → Methyl 3-[(e)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate

HRID 1371030

反応式

HRID 1371030 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.[CH2:21](Br)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:9]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH2:21]/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 98116BromomethylstyreneHCID 18510261Methyl 3-[2-(4-fluorophenyl)-2-oxoethyl]benzoate

生成物 1

HCID 18510225Methyl 3-[(e)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate収率 87.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the product from Step 1 (1.0 g, 3.7 mmol) and cinnamyl bromide (0.72 g, 3.7 mmol) in DMF (15 mL) at 0° C. under N2 was added the NaH (121 mg, 4.0 mmol, 80% in oil). After 20 min. at 0° C., the reaction was stirred for 1 h at r.t. Saturated NH4Cl (15 mL) was then added and the product was extracted with Et2O. The organic phase was washed with H2O and brine, and was then dried (MgSO4) filtered, and evaporated. The residue was purified by flash chromatography (1:10 EtOAc:hexane) to give a colourless oil (1.26 g).

後処理

  1. extractionthe product was extracted with Et2O
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialwas then dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (1:10 EtOAc:hexane)

出典と根拠

ORDレコード
ord-1f8e870885524a499154f697da8702ca
出典データセット
uspto-grants-2003_06
特許番号
US06583126B2

関連ノート

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