Potassium Carbonate → Ethyl 2-ethoxy-3-{3-[3-(4-methylsulfonyloxyphenyl)propoxy]phenyl}propanoate

HRID 987237Notes

Reaction equation

HRID 987237 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14]CS([O-])(=O)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH2:20]([O:22][C:23](=[O:36])[CH:24]([O:33][CH2:34][CH3:35])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=1)[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:20]([O:22][C:23](=[O:36])[CH:24]([O:33][CH2:34][CH3:35])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:14][CH2:13][CH2:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=2)[CH:27]=1)[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 229884243-(4-Methylsulfonyloxyphenyl)propylmethanesulfonateHCID 229884442-Ethoxy-3-(3-hydroxyphenyl)propanoic acid ethyl ester

Product 1

HCID 22988419Ethyl 2-ethoxy-3-{3-[3-(4-methylsulfonyloxyphenyl)propoxy]phenyl}propanoateYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-(4-Methanesulfonyloxyphenyl)propylmethanesulfonate (1.905 g; 6.18 mmole) dissolved in acetonitrile (13 ml) was added dropwise to a mixture of 2-ethoxy-3-(3-hydroxyphenyl)propanoic acid ethyl ester (1.47 g; 6.18 mmole) and potassium carbonate (2.56 g; 18.54 mmole) in acetonitrile (15 ml). The mixture was refluxed for 5 hours, then the solvent was evaporated in vacuo and water was added. The mixture was extracted twice with dichloromethane, dried (sodium sulfate), filtered and the solvent was evaporated in vacuo. Purification by chromatography on silica gel using diethyl ether/petroleum ether (gradient 33% to 100% diethyl ether) gave 1.80 g (yield 65%) of 2-ethoxy-3-{3-[3-(4-methanesulfonyloxyphenyl)propoxy]phenyl}propanoic acid ethyl ester.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customthe solvent was evaporated in vacuo and water
  3. additionwas added
  4. extractionThe mixture was extracted twice with dichloromethane
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customthe solvent was evaporated in vacuo
  8. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-0377117309a443adb4e29bf02b678a30
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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