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

HRID 1404159Notes

Reaction equation

HRID 1404159 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.C[O-].[Na+].Cl>CO>[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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 70922372methyl 1-(phenylsulfonyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 90405535methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of the product prepared in Step A (704 mg, 1.9 mmol, 1 eq) in methanol (10 mL) was added a solution of NaOMe in MeOH (2.46 mL of a 25% solution, 10.6 mmol, 5.6 eq). After 1 hr, 1 N HCl was added, the aqueous was extracted with diethyl ether, washed with brine, dried over MgSO4 and concentrated to yield methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylate.

Workup

  1. extractionthe aqueous was extracted with diethyl ether
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d6835deaf6ee42a28b0fd4dd64289f47
Source dataset
uspto-grants-2014_12
Patent number
US08912227B1

Reaction notes

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