Sodium hydride → (2E,4E)-Ethyl 4-(1-(benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-ylidene)but-2-enoate

HRID 1907746ノート

反応式

HRID 1907746 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:15][CH2:14][C:13](=O)[CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(OP([CH2:25]/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])(OCC)=O)C.[H-].[Na+]>COCCOC>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:15][CH2:14]/[C:13](=[CH:25]\[CH:26]=[CH:27]\[C:28]([O:30][CH2:31][CH3:32])=[O:29])/[CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 218216451-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-one

生成物 1

HCID 59737265(2E,4E)-Ethyl 4-(1-(benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-ylidene)but-2-enoate収率 16.1%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of ketone 274 (0.65 g, 2.96 mmol) and (E)-ethyl 4-(diethoxyphosphoryl)but-2-enoate (1.0 mL, 4.33 mmol) in ethyleneglycol dimethylether (50 mL) at 0° C. was added NaH (0.26 g, 6.58 mmol) and the mixture was stirred at 0° C. for 30 min then at room temperature for 2 h. The reaction mixture was quenched with acetone (2 mL) then diluted with DCM and washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (eluent: 50% AcOEt in DCM) to provide title compound 275 (0.15 g, 16% yield) as a mixture of cis/trans isomers.

後処理

  1. waitat room temperature for 2 h
  2. customThe reaction mixture was quenched with acetone (2 mL)
  3. additionthen diluted with DCM
  4. washwashed with saturated NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (eluent: 50% AcOEt in DCM)

出典と根拠

ORDレコード
ord-83ef5ee08ccc4614a7ec95a52f1ecf1d
出典データセット
uspto-grants-2013_12
特許番号
US08598168B2

反応ノート

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