Water → Ethyl 3-cyclopropyl-3-(2-methoxypyridin-4-yl)acrylate

HRID 709754Notes

Reaction equation

[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH:17]1([C:20]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH3:29])[CH:23]=2)=O)[CH2:19][CH2:18]1.O>C1COCC1>[CH:17]1([C:20]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH3:29])[CH:23]=2)=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:18][CH2:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, to a suspension of 60% sodium hydride (2.99 g) in THF (200 ml) was added ethyl diethylphosphonoacetate (29.7 mL) at 0° C., and the mixture was stirred at 0° C. for 5 min. To the obtained colorless solution was added cyclopropyl(2-methoxypyridin-4-yl)methanone (4.42 g) at 0° C., and the mixture was heated under reflux for 1 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound. This compound was used for the next step without further purification.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 1 hr
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-7ea54a7b3ef944689804b591f2cf46cb
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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