Boron trifluoride → 3-Methyl-5-oxooxolan-3-yl 2-methylprop-2-enoate

HRID 526801Notes

Reaction equation

HRID 526801 reaction equation
[C:1]([O:6][CH2:7][C:8]1(C)[O:12][C:10](=[O:11])[CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].B(F)(F)F.[CH3:18]OC1C=CC(O)=CC=1>C(OCC)(=O)C>[C:1]([O:6][C:7]1([CH3:18])[CH2:8][O:12][C:10](=[O:11])[CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 90154-MethoxyphenolHCID 72550462HCID 72550462, compound

Product 1

HCID 220262473-Methyl-5-oxooxolan-3-yl 2-methylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 50 mL four-necked flask, 0.5 g of β-methacryloyloxymethyl-β-methyl-β-propiolactone was put, and dissolved in 10 g of ethyl acetate, and a stirrer, a thermometer and a Dimroth cooling tube were connected thereto. Then, 5 mol % of diethyl ether complex of boron trifluoride was added thereto based on the substrate, and 5 mg of p-methoxyphenol was added thereto, and while solution temperature was kept at 30° C., the resulting mixture was stirred. After the mixture was stirred for 2 hours, the resulting reaction mixture was washed with a 10% sodium carbonate aqueous solution and saturated brine, and dried over magnesium sulfate. After separation by filtration, the solvent was distilled off using an evaporator. Consequently, 0.42 g of crude β-methacryloyloxy-β-methyl-γ-butyrolactone represented by formula (8) was obtained, and a quantitative isomerization reaction was confirmed by HPLC and NMR.

Workup

  1. temperaturea stirrer, a thermometer and a Dimroth cooling tube
  2. additionwas added
  3. customwas kept at 30° C.
  4. stirringAfter the mixture was stirred for 2 hours
  5. customthe resulting reaction mixture
  6. washwas washed with a 10% sodium carbonate aqueous solution and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customAfter separation
  9. filtrationby filtration
  10. distillationthe solvent was distilled off
  11. customan evaporator
  12. customwas obtained
  13. customa quantitative isomerization reaction

Sources & evidence

ORD record
ord-baa47cfefb7b4b8a9295fd0df56290a3
Source dataset
uspto-grants-2016_05
Patent number
US09346775B2

Reaction notes

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