Triethylamine → Ethyl 2-fluoro-3-(methacryloyloxy)pentanoate

HRID 576466Notes

Reaction equation

HRID 576466 reaction equation
C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[F:17][CH:18]([CH:24]([OH:27])[CH2:25][CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20].[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1COCC1>[F:17][CH:18]([CH:24]([O:27][C:28](=[O:32])[C:29]([CH3:31])=[CH2:30])[CH2:25][CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 79367479Ethyl 2-fluoro-3-hydroxypentanoate

Product 1

HCID 86684660Ethyl 2-fluoro-3-(methacryloyloxy)pentanoateYield 71.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, 50 mL of dehydrated THF, 4.63 g (45.8 mmol) of triethylamine and 0.466 g (3.82 mmol) of dimethylaminopyridine were added to 6.27 g (38.2 mmol) of the ethyl 2-fluoro-3-hydroxypentanoate at a room temperature. Thereafter, 4.39 g (42.0 mmol) of methacrylic acid chloride was added dropwise over 10 min, and then the mixture was stirred for 2 hrs. After disappearance of the raw material was confirmed by thin layer chromatography (TLC), an aqueous sodium bicarbonate solution was added to stop the reaction. Thereafter, ethyl acetate was added to the reaction liquid and extraction was carried out three times. The organic layer thus obtained was washed with water and saturated brine each once, and dried by adding anhydrous sodium sulfate. Thereafter, the product obtained by distilling off the solvent under a reduced pressure was purified by column chromatography to give 6.38 g (yield: 60%) of ethyl 2-fluoro-3-(methacryloyloxy)pentanoate represented by the following formula.

Workup

  1. customthe reaction
  2. customThe organic layer thus obtained
  3. washwas washed with water and saturated brine each once, and
  4. customdried
  5. additionby adding anhydrous sodium sulfate
  6. customThereafter, the product obtained
  7. distillationby distilling off the solvent under a reduced pressure
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-2018ad9d9b064401a4487d64e3428b8e
Source dataset
uspto-grants-2015_05
Patent number
US09040221B2

Reaction notes

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