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

HRID 428637Notes

Reaction equation

HRID 428637 reaction equation
[OH:1][CH:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1.ClCCl.C(N(CC)CC)C.[C:18](Cl)(=[O:22])[C:19]([CH3:21])=[CH2:20]>O>[C:18]([O:1][CH:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1)(=[O:22])[C:19]([CH3:21])=[CH2:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471Triethylamine3×HCID 13528Methacryloyl chloride3×HCID 956523,4-Dihydroxybutanoic acid gamma-lactone

Product 1

HCID 114010112-Propenoic acid, 2-methyl-, tetrahydro-5-oxo-3-furanyl esterYield 117.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-65 °C

Procedure

In a glass flask equipped with a stirrer, two dropping funnels, a thermometer and a Dimroth condenser, β-hydroxy-γ-butyrolactone (91.1 g, 0.875 mol) having a purity of 98% obtained by repeating the process of Example 1 and 500 ml of dry dichloromethane were charged, and then triethylamine (117.5 g, 1.16 mol) was charged in one dropping funnel and methacrylic acid chloride (112 g, 1.071 mol) was charged in another dropping funnel. The atmosphere in the glass flask was replaced by nitrogen and then cooled to −60 to −70° C. in a dry ice-acetone bath. While stirring in the glass flask, triethylamine and methacrylic acid chloride were added dropwise with adjusting so that the amount of triethylamine becomes small excess to that of methacrylic acid chloride. After the completion of the dropwise addition, stirring was continued for 3 hours. To the reaction solution, 300 ml of water was added and a small amount of Celite was added, followed by filtration. The filtrate was washed three times with 300 ml of water using a separatory funnel and dried by adding 80 g of magnesium sulfate and, after filtering, the filtrate was concentrated to obtain 175 g of crude β-methacryloyloxy-γ-butyrolactone. This β-methacryloyloxy-γ-butyrolactone was purified by silica gel column chromatography to obtain β-methacryloyloxy-γ-butyrolactone (106.3 g, 0.625 mol).

Workup

  1. customIn a glass flask equipped with a stirrer
  2. customobtained
  3. additionwere charged
  4. additionwas charged in another dropping funnel
  5. additionwere added dropwise
  6. additionAfter the completion of the dropwise addition
  7. additiona small amount of Celite was added
  8. filtrationfollowed by filtration
  9. washThe filtrate was washed three times with 300 ml of water using a separatory funnel
  10. customdried
  11. additionby adding 80 g of magnesium sulfate
  12. filtrationafter filtering
  13. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5182d25fd9674c9b8ad8d4879829c13e
Source dataset
uspto-grants-2001_11
Patent number
US06313321B1

Reaction notes

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