1-Ethoxycarbonyl-1,1-difluoro-2-butyl methacrylate → Methyl 2,2-difluoro-3-(methacryloyloxy)pentanoate

HRID 1025253Notes

Reaction equation

HRID 1025253 reaction equation
[F:1][C:2]([F:17])([CH:8]([O:11][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14])[CH2:9][CH3:10])[C:3]([O:5][CH2:6]C)=[O:4]>CO>[F:1][C:2]([F:17])([CH:8]([O:11][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14])[CH2:9][CH3:10])[C:3]([O:5][CH3:6])=[O:4]

Participants

3

Reactant 1

HCID 598638611-Ethoxycarbonyl-1,1-difluoro-2-butyl methacrylate

Product 1

HCID 59482687Methyl 2,2-difluoro-3-(methacryloyloxy)pentanoateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 g of ethyl 2,2-difluoro-3-(methacryloyloxy)pentanoate was dissolved in 1000 g of dehydrated methanol in a nitrogen atmosphere. After the addition of 0.1 g of N,N-dimethylaminopyridine (DMAP), the mixture was heated and refluxed for 5 hours. After evaporating the solvent, the residue was dissolved in 1000 g of dehydrated methanol, and the mixture was heated and refluxed for 5 hours. After evaporating the solvent, the residue was dissolved in 300 g of n-hexane. The solution was filtered through 50 g of silica gel to remove DMAP. 89.7 g of methyl 2,2-difluoro-3-(methacryloyloxy)pentanoate (M-29) was thus obtained (yield: 95%).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 5 hours
  3. customAfter evaporating the solvent
  4. dissolutionthe residue was dissolved in 1000 g of dehydrated methanol
  5. temperaturethe mixture was heated
  6. temperaturerefluxed for 5 hours
  7. customAfter evaporating the solvent
  8. dissolutionthe residue was dissolved in 300 g of n-hexane
  9. filtrationThe solution was filtered through 50 g of silica gel
  10. customto remove DMAP

Sources & evidence

ORD record
ord-238f41ab35d742fbacac452acdd49f9a
Source dataset
uspto-grants-2014_05
Patent number
US08728706B2

Reaction notes

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