Water → Ethyl 3-cyclopropyl-3-(2-((methoxymethoxy)methyl)pyridin-4-yl)acrylate

HRID 1049475Notes

Reaction equation

HRID 1049475 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]([CH2:28][O:29][CH2:30][O:31][CH3:32])[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]([CH2:28][O:29][CH2:30][O:31][CH3:32])[CH:23]=2)=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 117759859Cyclopropyl(2-((methoxymethoxy)methyl)pyridin-4-yl)methanone

Product 1

HCID 131736013Ethyl 3-cyclopropyl-3-(2-((methoxymethoxy)methyl)pyridin-4-yl)acrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 60% sodium hydride (1.09 g) in THF (30 mL) was added ethyl diethylphosphonoacetate (6.46 mL) at 0° C., and then cyclopropyl(2-((methoxymethoxy)methyl)pyridin-4-yl)methanone (1.20 g) was added. The reaction mixture was heated under reflux for 2 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 and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.36 g) as a pale-yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e8183125da6d486797f7a1c65148635a
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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