Diethyl fluoromalonate → HCID 15176477, compound

HRID 1665670Notes

Reaction equation

HRID 1665670 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:14])[CH:7]([F:13])[C:8]([O:10]CC)=[O:9])C>CO>[CH3:3][O:5][C:6](=[O:14])[CH:7]([F:13])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 12702Diethyl fluoromalonateHCID 14797Potassium Hydroxide

Product 1

HCID 15176477HCID 15176477, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

KOH (38 mg, 0.67 mmol) was added to a solution 2-fluoro-malonic acid diethyl ester (100 mg, 0.563 mmol) in methanol (0.7 mL). The reaction mixture was stirred for 4 hours at ambient temperature then concentrated. The residue was diluted with water, acidified with conc. HCl, and the product was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford 70 mg (77%) of 2-fluoro-malonic acid monomethyl ester

Workup

  1. concentrationthen concentrated
  2. additionThe residue was diluted with water
  3. extractionthe product was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1df3aa2a4c343029aa555a578f84828
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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