Sodium hydride → N,N-diethyl (E)-3-[3-allyl-4-(1-phenylethoxy)-phenyl]-but-2-enamide

HRID 1596717ノート

反応式

HRID 1596717 の反応式
[H-].[Na+].[CH2:3]([N:5]([CH2:15][CH3:16])[C:6](=[O:14])[CH2:7]P(=O)([O-])OCC)[CH3:4].[CH2:17]([C:20]1[CH:21]=[C:22]([C:35](=O)[CH3:36])[CH:23]=[CH:24][C:25]=1[O:26][CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:28])[CH:18]=[CH2:19]>C1COCC1>[CH2:15]([N:5]([CH2:3][CH3:4])[C:6](=[O:14])/[CH:7]=[C:35](/[C:22]1[CH:23]=[CH:24][C:25]([O:26][CH:27]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH3:28])=[C:20]([CH2:17][CH:18]=[CH2:19])[CH:21]=1)\[CH3:36])[CH3:16]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 106841633'-Allyl-4'-(1-phenylethoxy)-acetophenoneHCID 86757414Ethyl [2-(diethylamino)-2-oxoethyl]-phosphonate

生成物 1

HCID 86757413N,N-diethyl (E)-3-[3-allyl-4-(1-phenylethoxy)-phenyl]-but-2-enamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 3′-allyl-4′-hydroxyacetophenone (3.46 g, 19.66), (1-bromoethyl)-benzene (3.05 mL, 21.63 mmol)), and K2CO3 (4.07 g, 29.49 mmol) in acetone (100 mL) is refluxed 20 hours. The mixture is then filtered and the filtrate is concentrated in vacuo. The residue is dissolved in EtOAc (100 mL) and then washed with H2O (1×100 mL) and brine (1×100 mL), dried over MgSO4, and concentrated in vacuo. Chromatography (5:1 hexane/EtOAc) yields 3′-allyl-4′-(1-phenylethoxy)-acetopbenone. To a solution of sodium hydride (0.54 g, 13.5 mmol) in THF (20 mL) is added a solution of ethyl [2-(diethylamino)-2-oxoethyl]-phosphonate (3.13 g. 12.5 mmol) in THF (20 ml). After stirring this mixture for 5 minutes. at room temperature, a solution of 3′-allyl-4′-(1-phenylethoxy)-acetophenone (2.91 g, 10.4 mmol) in ThF (30 mL) is added, and the solution is refluxed 18 hours. After cooling, the mixture is then quenched with saturated aqueous ammonium chloride (50 mL), and extracted with ethyl acetate (4×75 mL). The combined organic phase is washed with water (1×100 mL) and brine (1×100 mL), dried over MgSO4, concentrated in vacuo, chromatographed (silica, 2:1 EtOAc/hexane) to yield N,N-diethyl (E)-3-[3-allyl 4-(1-phenylethoxy)-phenyl)-but-2-enamide.

後処理

  1. temperaturethe solution is refluxed 18 hours
  2. temperatureAfter cooling
  3. customthe mixture is then quenched with saturated aqueous ammonium chloride (50 mL)
  4. extractionextracted with ethyl acetate (4×75 mL)
  5. washThe combined organic phase is washed with water (1×100 mL) and brine (1×100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customchromatographed (silica, 2:1 EtOAc/hexane)

出典と根拠

ORDレコード
ord-193c8bf3d6d849099ca8df2e732a33d6
出典データセット
uspto-grants-2001_09
特許番号
US06291530B1

反応ノート

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