Potassium Carbonate → Ethyl 2-ethoxy-3-[3-methyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]propanoate

HRID 353307

Reaction equation

HRID 353307 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:18])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[CH3:19][S:20]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31]OS(C)(=O)=O)=[CH:26][CH:25]=1)(=[O:22])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:31][CH2:30][C:27]2[CH:26]=[CH:25][C:24]([O:23][S:20]([CH3:19])(=[O:21])=[O:22])=[CH:29][CH:28]=2)=[C:13]([CH3:18])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112201221-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethaneHCID 22708451Ethyl 2-ethoxy-3-(4-hydroxy-3-methylphenyl)propanoate

Product 1

HCID 22708415Ethyl 2-ethoxy-3-[3-methyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]propanoateYield 59.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Ethyl 2-ethoxy-3-(4-hydroxy-3-methylphenyl)propanoate (0.27 g, 1.05 mmole) and 4-{2-[(methylsulfonyl)oxy]ethyl}phenyl methanesulfonate (0.62 g, 2.11 mmole) were dissolved in 2-butanone (10 ml). Polyethyleneglycol 400 (0.20 g) and anhydrous potassium carbonate (0.22 g, 1.58 mmole) were added the mixture. After stirring at reflux for 16 hours it was checked with 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, 7 μm, 50×250 mm) using actonitrile(60-80%) in ammonium acetate buffer (pH 7) as mobile phase gave 0.28 g (54% 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, 7 μm, 50×250 mm)

Sources & evidence

ORD record
ord-02697ed671954d6796654a028d818447
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Linked notes

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