Diethyl fluoromalonate → HCID 13350490, compound

HRID 1847018Notes

Reaction equation

HRID 1847018 reaction equation
[F:1][CH:2]([C:8]([O:10]CC)=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH-].[K+]>C(O)C>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([F:1])[C:8]([OH:10])=[O:9])[CH3:7]

Participants

4

Reactant 2

HCID 12702Diethyl fluoromalonateHCID 14797Potassium Hydroxide

Product 1

HCID 13350490HCID 13350490, compoundYield 114.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl fluoromalonate (15.0 g, 84.19 mmol) was suspended in ethanol (50 ml), a solution of potassium hydroxide (5.56 g, 84.19 mmol) in ethanol (50 ml) was added dropwise under cooling on ice and the mixture was stirred at room temperature for 14 hours. The solvent was removed under reduced pressure, the residue was dissolved in water and acidified by adding a 6N hydrochloric acid aqueous solution under cooling on ice. The mixture was extracted with diethyl ether and the extract was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to yield 14.42 g of a crude product of the title compound in the form of a colorless clear oily product.

Workup

  1. temperatureunder cooling on ice
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. additionby adding a 6N hydrochloric acid aqueous solution
  5. temperatureunder cooling on ice
  6. extractionThe mixture was extracted with diethyl ether
  7. dry with materialthe extract was dried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9b4287cfd4e7483793b17dd61acf556c
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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