methyl 1-(phenylsulfonyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate → methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 1404181

Reaction equation

HRID 1404181 reaction equation
C1(S([N:10]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[C:11]2[C:19]([O:21][CH3:22])=[O:20])(=O)=O)C=CC=CC=1.[F:23][C:24]([F:47])([C:29]1[CH:33]=[CH:32][N:31]([S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:30]=1[C:43]([O:45][CH3:46])=[O:44])[C:25]([F:28])([F:27])[F:26].O(C)[Na]>O1CCCC1>[F:18][C:15]([F:16])([F:17])[C:12]1[CH:13]=[CH:14][NH:10][C:11]=1[C:19]([O:21][CH3:22])=[O:20].[F:47][C:24]([F:23])([C:29]1[CH:33]=[CH:32][N:31]([S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:30]=1[C:43]([O:45][CH3:46])=[O:44])[C:25]([F:28])([F:27])[F:26]

Participants

6

Reactant 3

HCID 70922372methyl 1-(phenylsulfonyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylateHCID 90406470methyl 3-(perfluoroethyl)-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylateHCID 178418582HCID 178418582, compound

Product 2

HCID 90405535methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylateHCID 90406470methyl 3-(perfluoroethyl)-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 100-mL round-bottom flask, was placed methyl 1-(benzenesulfonyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate and methyl 3-(perfluoroethyl)-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate (1.8 g, 5.40 mmol, 1.00 equiv) and tetrahydrofuran (15.0 mL). To the resulting mixture was then added NaOCH3 (1.17 g, 21.67 mmol, 4.01 equiv), in portions at 0° C. The resulting solution was stirred for 30 min at 0° C. in a water/ice bath. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 2N hydrogen chloride until the solution became clear. The resulting solution was extracted with ethyl acetate (3×20 mL) and the organic layers combined. The resulting mixture was washed with sodium chloride (1×20 mL). The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to yield methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylate and methyl 3-(perfluoroethyl)-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate as a yellow solid. The yellow soli, was used in the next step without further purification.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customat 0° C
  3. customThe reaction was then quenched by the addition of 2N hydrogen chloride until the solution
  4. extractionThe resulting solution was extracted with ethyl acetate (3×20 mL)
  5. washThe resulting mixture was washed with sodium chloride (1×20 mL)
  6. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-881408bdbe8d42238e989ce778fa19c7
Source dataset
uspto-grants-2014_12
Patent number
US08912227B1

Linked notes

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