Ethyl fluoroacetate → HCID 9728, compound

HRID 1035929Notes

Reaction equation

HRID 1035929 reaction equation
[F:1][CH2:2][C:3](OCC)=O.[H-].C([Al+]CC(C)C)C(C)C.[C:18]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:20][CH2:21][CH3:22])=[O:19]>C(Cl)Cl>[F:1][CH2:2][CH:3]=[CH:23][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 9988Ethyl fluoroacetateHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 9728HCID 9728, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 2-fluoroacetate (21.0 g) in CH2Cl2 (200 mL) at −78° C. was treated dropwise over 45 min with a 1.0 M solution of diisobutylaluminum hydride in CH2Cl2 (200 mL) maintaining the internal temperature below −70° C. Stirring was continued at −78° C. for 30 minutes and then (carbethoxymethylene)triphenylphosphorane (70.0 g) was added in one portion. The reaction mixture was allowed to slowly reach room temperature while stirring overnight. It was then quenched with methanol, filtered and concentrated to give the product as a mixture of isomers (E/Z=3:1).

Workup

  1. temperaturemaintaining the internal temperature below −70° C
  2. customwas allowed to slowly reach room temperature
  3. stirringwhile stirring overnight
  4. customIt was then quenched with methanol
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the product
  8. additionas a mixture of isomers (E/Z=3:1)

Sources & evidence

ORD record
ord-7b8d6f3672f44affb9bc63352ffcb504
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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