Potassium Carbonate → Ethyl 3-[3-benzyl-4-({4-[(methylsulfonyl)oxy]phenethyl}oxy)phenyl]-2-ethoxypropanoate

HRID 353297

Reaction equation

HRID 353297 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH2:15][CH:16]([O:22][CH2:23][CH3:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=[CH:12][C:13]=1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37]OS(C)(=O)=O)=[CH:32][CH:31]=1)(=[O:28])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([C:8]1[CH:9]=[C:10]([CH2:15][CH:16]([O:22][CH2:23][CH3:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=[CH:12][C:13]=1[O:14][CH2:37][CH2:36][C:33]1[CH:32]=[CH:31][C:30]([O:29][S:26]([CH3:25])(=[O:27])=[O:28])=[CH:35][CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112201221-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethaneHCID 22708450Ethyl 3-(3-benzyl-4-hydroxyphenyl)-2-ethoxypropanoate

Product 1

HCID 22708421Ethyl 3-[3-benzyl-4-({4-[(methylsulfonyl)oxy]phenethyl}oxy)phenyl]-2-ethoxypropanoateYield 36.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Ethyl 3-(3-benzyl-4-hydroxyphenyl)-2-ethoxypropanoate (0.50 g, 3.73 mmole) and 4-{2-[(methylsulfonyl)oxy]ethyl}phenyl methanesulfonate (2.20 g, 7.46 mmole) were dissolved in 2-butanone (20 ml). Polyethyleneglycol 400 (0.20 g) and anhydrous potassium carbonate (0.78 g, 5.59 mmole) were added the mixture. After stirring at reflux for 16 hours it was checked using HPLC whether all the starting material was consumed. The mixture was washed with water dried with magnesium sulfate and evaporated. Purification of the crude product with preparative HPLC (Kromasil C8, 10 μm, 50×500 mm) using acetonitrile (60-80%) in ammonium acetate buffer (pH 7) as mobile phase gave 0.71 g (36% yield) of the desired product

Workup

  1. temperatureat reflux for 16 hours it
  2. customwas consumed
  3. washThe mixture was washed with water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customPurification of the crude product with preparative HPLC (Kromasil C8, 10 μm, 50×500 mm)

Sources & evidence

ORD record
ord-611ec8b2deb145b3809eea8a5787ca5a
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Linked notes

Loading…