Methyl Methacrylate → HCID 19366821, compound

HRID 849531Notes

Reaction equation

HRID 849531 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](S)=[CH:5][CH:4]=1.[C:10]([O:15]C)(=[O:14])[C:11]([CH3:13])=[CH2:12].[CH2:17](N(CC)CC)C.[S:24]([O-:29])(O[O-])(=O)=[O:25].[K+].[K+]>CO.O>[CH3:13][CH:11]([CH:12]([S:24]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:29])=[O:25])[CH3:17])[C:10]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 6658Methyl MethacrylateHCID 8471TriethylamineHCID 127654-MethoxybenzenethiolHCID 10313463Potassium peroxymonosulphate

Product 1

HCID 19366821HCID 19366821, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Part A: To a solution of 2.6 g (18 mmol) of 4-methoxybenzenethiol in 30 ml of methanol at zero° C., was added 2.2 mL (2.0 g, 20 mmol) of methyl methacrylate. After nitrogen gas was bubbled through the solution for 15 min., 2.8 mL (2.1 g, 20 mmole) of triethylamine was added. After 4.5 hours, 20 mL of methanol and 10 mL of water were added, followed by 36 g (59 mmol) of potassium peroxymonosulfate (OXONE®). After 65 hours, the reaction was filtered, the filter cake was washed with methanol and the filtrate concentrated in vacuo, ethyl acetate and water were added, the layers were separated and the aqueous layer was extracted 2×s with ethyl acetate. The 3 organic extracts were combined and washed with saturated sodium bicarbonate solution and brine, dried with magnesium sulfate, filtered and concentrated to afford 4.1 g of crude product. This was chromatographed on silica gel using 25%-35% ethyl acetate/hexane to yield 3.5 g of pure methyl 3-[(4-methoxyphenyl)sulfonyl]-butanoic acid, m/z=279 (M+Li).

Workup

  1. customAfter nitrogen gas was bubbled through the solution for 15 min.
  2. waitAfter 65 hours
  3. filtrationthe reaction was filtered
  4. washthe filter cake was washed with methanol
  5. concentrationthe filtrate concentrated in vacuo, ethyl acetate and water
  6. additionwere added
  7. customthe layers were separated
  8. extractionthe aqueous layer was extracted 2×
  9. washwashed with saturated sodium bicarbonate solution and brine
  10. dry with materialdried with magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto afford 4.1 g of crude product
  14. customThis was chromatographed on silica gel using 25%-35% ethyl acetate/hexane

Sources & evidence

ORD record
ord-15be52817f7c4b0280bdf287d888bbfa
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

Loading…