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Boron trifluoride → 2-Propenoic acid, 2-methyl-, tetrahydro-5-oxo-3-furanyl ester

HRID 526804
Notes
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Reaction equation

HRID 526804 reaction equation
[C:1]([O:6][CH2:7][CH:8]1[O:12][C:10](=[O:11])[CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].B(F)(F)F>C1(C)C=CC=CC=1>[C:1]([O:6][CH:7]1[CH2:8][O:12][C:10](=[O:11])[CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6356Boron trifluorideHCID 57796750beta-Methacryloyloxymethyl-beta-propiolactone

Product 1

HCID 114010112-Propenoic acid, 2-methyl-, tetrahydro-5-oxo-3-furanyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

In a 20 mL Schlenk flask, 2.0 g of crude β-methacryloyloxymethyl-β-propiolactone was put, and dissolved in 8.0 g of toluene. Further, 54 μL of diethyl ether complex of boron trifluoride was added thereto, and the resulting mixture was warmed to 30° C. and stirred. After the mixture was stirred for 2 hours, the resulting reaction mixture was washed with a 10% sodium hydrogen carbonate aqueous solution and saturated brine, and dried over magnesium sulfate. After separation by filtration, the solvent was distilled off using an evaporator to give 1.1 g of crude β-methacryloyloxy-γ-butyrolactone represented by formula (10). FIG. 3 shows an NMR measurement chart.

Workup

  1. stirringAfter the mixture was stirred for 2 hours
  2. customthe resulting reaction mixture
  3. washwas washed with a 10% sodium hydrogen carbonate aqueous solution and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter separation
  6. filtrationby filtration
  7. distillationthe solvent was distilled off
  8. customan evaporator

Sources & evidence

ORD record
ord-64390162edaf468e91ddd3c8a63dff37
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346775B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes