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

HRID 1907746Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-83ef5ee08ccc4614a7ec95a52f1ecf1d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598168B2

Reaction notes

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