Triethylamine → ethyl (E)-3-(3-ethoxy-4-trifluoromethanesulfonyloxyphenyl)-2-methylacrylate

HRID 390653Notes

Reaction equation

HRID 390653 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[CH2:16]([O:18][C:19]1[CH:20]=[C:21](/[CH:26]=[C:27](\[CH3:33])/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:22]=[CH:23][C:24]=1O)[CH3:17].C(N(CC)CC)C>ClCCl.C(=O)([O-])O.[Na+]>[CH2:16]([O:18][C:19]1[CH:20]=[C:21](/[CH:26]=[C:27](\[CH3:33])/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:22]=[CH:23][C:24]=1[O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86626101ethyl (E)-3-(3-ethoxy-4-hydroxyphenyl)-2-methylacrylate

Product 1

HCID 86626100ethyl (E)-3-(3-ethoxy-4-trifluoromethanesulfonyloxyphenyl)-2-methylacrylateYield 107.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

0.8 mL (4.8 mmol) of triflic anhydride is added to a solution of 1.5 g (4 mmol) of ethyl (E)-3-(3-ethoxy-4-hydroxyphenyl)-2-methylacrylate and 1.6 mL (12 mmol) of triethylamine in 20 mL of dichloromethane at 0° C. The reaction mixture is stirred at room temperature for 1 hour. The medium is hydrolyzed in sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over magnesium sulfate. The solvent is evaporated off and 1.65 g (100%) of ethyl (E)-3-(3-ethoxy-4-trifluoromethanesulfonyloxyphenyl)-2-methylacrylate are obtained in the form of a brown oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-37284d47693b4206a0db2898508476fb
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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