Trifluoroacetic acid → (E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid

HRID 1931042Notes

Reaction equation

HRID 1931042 reaction equation
C([O:5][C:6](=[O:24])/[CH:7]=[CH:8]/[C:9]1[CH:13]=[CH:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:20]1([CH3:23])[CH:19]=[CH:18][C:17]([S:14]([N:11]2[CH:12]=[CH:13][C:9](/[CH:8]=[CH:7]/[C:6]([OH:24])=[O:5])=[CH:10]2)(=[O:15])=[O:16])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66646193(E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester2×

Product 1

HCID 66646287(E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acidYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.60 g of (E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester (compound C1) are dissolved in 70 ml of dichloromethane at ambient temperature. Then 7 ml of trifluoroacetic acid (TFA) are added and stirred for 4 hours. The solvent is evaporated to dryness and to the residue are added 30 ml of water. The water phase is extracted exhaustively with ethyl acetate. Then the organic phase is dried over sodium sulfate. The filtrate is evaporated and dried under vacuo to give 0.951 g of the title compound as a pale grey solid.

Workup

  1. customThe solvent is evaporated to dryness and to the residue
  2. additionare added 30 ml of water
  3. extractionThe water phase is extracted exhaustively with ethyl acetate
  4. dry with materialThen the organic phase is dried over sodium sulfate
  5. customThe filtrate is evaporated
  6. customdried under vacuo

Sources & evidence

ORD record
ord-2bd0da54c4b04bf99e15502986d17beb
Source dataset
uspto-grants-2012_05
Patent number
US08188138B2

Reaction notes

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