Potassium Carbonate → Ethyl 3-[3-tert-butyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoate

HRID 353300

Reaction equation

HRID 353300 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([O:19][CH2:20][CH3:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34]OS(C)(=O)=O)=[CH:29][CH:28]=1)(=[O:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([O:19][CH2:20][CH3:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[CH:9][C:10]=1[O:11][CH2:34][CH2:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][S:23]([CH3:22])(=[O:24])=[O:25])=[CH:32][CH:31]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112201221-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethaneHCID 22708416Ethyl 3-(3-tert-butyl-4-hydroxyphenyl)-2-ethoxypropanoate

Product 1

HCID 10300195Ethyl 3-[3-tert-butyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoateYield 22.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Ethyl 3-(3-tert-butyl-4-hydroxyphenyl)-2-ethoxypropanoate (0.15 g, 0.44 mmole) and 4-{2-[(methylsulfonyl)oxy]ethyl}phenyl methanesulfonate (0.26 g, 0.89 mmole) were dissolved in 2-butanone (4 ml). Polyethyleneglycol 400 (0.05 g) and anhydrous potassium carbonate (0.092 g, 0.67 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, 7 μm, 50×250 mm) using actonitrile(40-80%) in ammonium acetate buffer (pH 7) as mobile phase gave 0.048 g (22% 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-4cada9979f354ec8bfeed55abff49f4d
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Linked notes

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