Trifluoromethanesulfonic anhydride → HCID 87491673, compound

HRID 2243496Notes

Reaction equation

HRID 2243496 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH:12]=[CH:13][C:7]=2[C:6]=1[OH:20])=[O:4].[O:21](S(C(F)(F)F)(=O)=O)[S:22]([C:25]([F:28])([F:27])[F:26])(=O)=[O:23]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH:12]=[CH:13][C:7]=2[C:6]=1[O:20][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:23])=[O:21])=[O:4]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 54718316HCID 54718316, compound

Product 1

HCID 87491673HCID 87491673, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-benzo[b]thiophene-2,6-dicarboxylic acid 6-allyl ester 2-methyl ester (3.2 g, 10.95 mmol) in DCM (50 mL) was added TEA (1.83 mL, 13.14 mmol), Tf2O (2.2 mL, 13.14 mL) and DMAP (67 mg, 0.55 mmol) at 0° C. The temperature was allowed to rise to room temperature and the resultant mixture was stirred for 4 hours, washed with aq. NaHCO3 and dried over MgSO4. The crude product was purified on CombiFlash column eluted with hexanes/EtOAc to give desire product, 3-trifluoromethanesulfonyloxy-benzo[b]thiophene-2,6-dicarboxylic acid 6-allyl ester 2-methyl ester as a white solid (3.88g, 84%).

Workup

  1. customto rise to room temperature
  2. washwashed with aq. NaHCO3
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified on CombiFlash column
  5. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-94123c75f66143c090573a5834081506
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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