Hydrochloric Acid → methyl 4-fluoro-3-oxopentanoate

HRID 1250993Notes

Reaction equation

HRID 1250993 reaction equation
[H-].[Na+].[F:3][CH:4]([CH3:9])[C:5](OC)=[O:6].[C:10]([O:13][CH3:14])(=[O:12])[CH3:11].Cl>>[F:3][CH:4]([CH3:9])[C:5](=[O:6])[CH2:11][C:10]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6584Methyl AcetateHCID 24758Sodium hydrideHCID 11083845METHYL 2-FLUOROPROPIONATE

Product 1

HCID 9793838methyl 4-fluoro-3-oxopentanoateYield 92%

Conditions

Temperature
32.5 °C

Procedure

To a liquid in which 1.31 g of a 62.8% sodium hydride had been suspended in 10 ml of tetrahydrofaran was added dropwise a mixed solution of 2.00 g of methyl 2-fluoropropionate and 2.10 g of methyl acetate over 10 minutes, and the mixture was then heated at 30 to 35° C. for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, neutralized with 1N-hydrochloric acid, and subjected to liquid separation. When the organic layer was quantitated by the gas chromatography internal standard method. As a result, it was found that 2.57 g of methyl 4-fluoro-3-oxopentanoate was formed (yield: 92%). When this organic layer was concentrated under reduced pressure and then distilled under reduced pressure, 2.03 g of methyl 4-fluoro-3-oxopentanoate could be obtained.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customsubjected to liquid separation
  4. customwas formed (yield: 92%)
  5. concentrationWhen this organic layer was concentrated under reduced pressure
  6. distillationdistilled under reduced pressure, 2.03 g of methyl 4-fluoro-3-oxopentanoate
  7. customcould be obtained

Sources & evidence

ORD record
ord-3ef10922e5d64660928af48f33324528
Source dataset
uspto-grants-2002_01
Patent number
US06340757B1

Reaction notes

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