Hydrochloric Acid → Ethyl 2-(3,5-difluorophenyl)-3-hydroxy-2-propenoate

HRID 133180Notes

Reaction equation

HRID 133180 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].[Na+].Cl.[CH:18](OCC)=[O:19]>>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[CH:18][OH:19])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 11481060Ethyl 2-(3,5-difluorophenyl)acetate

Product 1

HCID 67388060Ethyl 2-(3,5-difluorophenyl)-3-hydroxy-2-propenoate

Procedure

5.0 g of ethyl 3,5-difluorophenylacetate are dissolved in 50 ml of ethyl formate. 2.0 g of 60% NaH are added portionwise. The mixture is poured onto a 1N HCl solution and then extraction is carried out with AcOEt. The residue is triturated in petroleum ether, the remaining white precipitate is filtered off and then the filtrate is evaporated to produce 3.3 g of the expected compound in the form of a liquid.

Workup

  1. extractionextraction
  2. customThe residue is triturated in petroleum ether
  3. filtrationthe remaining white precipitate is filtered off
  4. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-dab81ae7a179419f995200fdce64b5a8
Source dataset
uspto-grants-2008_06
Patent number
US07390818B2

Reaction notes

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