18-Crown-6 → HCID 19063422, compound

HRID 1900150Notes

Reaction equation

HRID 1900150 reaction equation
[C:1](=[O:10])([O:7][CH2:8]Cl)[O:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:11]([O-:16])(=[O:15])[C:12]([CH3:14])=[CH2:13].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[C:1](=[O:10])([O:7][CH2:8][O:16][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])[O:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 15256996Butyl chloromethyl carbonateHCID 23667354Potassium methacrylate

Product 1

HCID 19063422HCID 19063422, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The intermediate n-butyl chloromethyl carbonate (2.5 g 15.0 mmol) was dissolved in dimethyl formamide (80 ml), and potassium methacrylate (1.77 g, 15.0 mmol) was added together with a catalytic amount of 18-crown-6 (0.2 g, 7.5 mmol). After 3 days at 25° C. the solvent was removed under reduced pressure, cholorform (30 ml) and water (20 ml) were added and the product was extracted into chloroform. The solvent was removed under reduced pressure after drying (MgSO4). Flash chromatography gave 1.96 g (61%) of butyl methacryloyloxymethyl carbonate.

Workup

  1. customAfter 3 days at 25° C. the solvent was removed under reduced pressure, cholorform (30 ml) and water (20 ml)
  2. additionwere added
  3. extractionthe product was extracted into chloroform
  4. customThe solvent was removed under reduced pressure
  5. dry with materialafter drying (MgSO4)

Sources & evidence

ORD record
ord-a8fc3731810343ad979c88a2ef36f72d
Source dataset
uspto-grants-1996_11
Patent number
US05574097

Reaction notes

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