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

HRID 1907746노트

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HRID 1907746 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-83ef5ee08ccc4614a7ec95a52f1ecf1d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598168B2

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