Potassium Phosphate, Dibasic → ethyl 4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 623777Notes

Reaction equation

HRID 623777 reaction equation
[F:1][C:2]([F:8])([F:7])S(Cl)(=O)=O.[CH2:9]([O:11][C:12]([C:14]1[NH:15][CH:16]=[C:17]([CH3:19])[CH:18]=1)=[O:13])[CH3:10].OP([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOC(C)=O.O>[CH3:19][C:17]1[CH:18]=[C:14]([C:12]([O:11][CH2:9][CH3:10])=[O:13])[NH:15][C:16]=1[C:2]([F:8])([F:7])[F:1]

Participants

7

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 79000Trifluoromethanesulfonyl chlorideHCID 643361Ethyl 4-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 71502098ethyl 4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylateYield 71.13%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonyl chloride (40.7 mL, 381.67 mmol) was added to the argon degassed solution of ethyl-4-methyl-1H-pyrrole-2-carboxylate (40 g, 254.45 mmol), K2HPO4 (132.9 g, 763.35 mmol), dichlorotris(1,10-phenanthroline) ruthenium (II) hydrate (3.6 g, 5.08 mmol) in acetonitrile. The reaction mixture was stirred for 6 d at room temperature adjacent to a fluorescent light bulb (23 W). The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×700 mL). Combined organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to yield crude mass which was then purified by column chromatography (100-200 mesh Silica gel; 20% ethyl acetate/hexane; Rff-value 0.7) to afford title compound (25 g, 71.13% yield, white color solid).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (2×700 mL)
  2. dry with materialCombined organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto yield crude mass which
  5. customwas then purified by column chromatography (100-200 mesh Silica gel; 20% ethyl acetate/hexane; Rff-value 0.7)

Sources & evidence

ORD record
ord-9dc1cf21e01e44d29b1ec13a8b78558e
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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