Chloroform → HCID 12505696, compound

HRID 1882345Notes

Reaction equation

HRID 1882345 reaction equation
C(Cl)(Cl)Cl.[CH3:5][C:6](=[CH:11]OS(C1C=CC(C)=CC=1)(=O)=O)[C:7]([O:9][CH3:10])=[O:8].[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>COC(C)(C)C>[CH3:11][C:6](=[CH:5][S:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7969ThiophenolHCID 8471TriethylamineHCID 85441230HCID 85441230, compound

Product 1

HCID 12505696HCID 12505696, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

To chloroform (100 mL) were added methyl 2-methyl-3-(p-toluenesulfonyloxy)acrylate (11.0 g) and thiophenol (6.3 g), and then added dropwise triethylamine (33 mL), and the mixture was stirred at 50° C. for 9 hours. To the reaction mixture were added tert-butyl methyl ether, and then a 1N aqueous sodium hydroxide solution, thereby layers were separated. The organic layer was washed with a saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain methyl 2-methyl-3-(phenylthio)acrylate (6.5 g).

Workup

  1. customa 1N aqueous sodium hydroxide solution, thereby layers were separated
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f9b7bf7591174acb898c4c9ee46d554e
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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