Hydrochloric Acid → HCID 86711836, compound

HRID 623748Notes

Reaction equation

HRID 623748 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:9]1[C:21]([O:23]CC)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>[OH-].[Na+]>[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:9]1[C:21]([OH:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 86711835HCID 86711835, compound

Product 1

HCID 86711836HCID 86711836, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

Ethyl 1-benzyl-3-(4-fluorophenyl)-4-methyl-1H-pyrrole-2-carboxylate (5.0 g, 14.83 mmol) was added to a solution of 8M NaOH (30 mL) and catalytic amount of TBAF (0.5 mL) at 0° C. The resulting mixture was stirred at 110° C. for 24 h. The reaction mixture was cooled to 0° C., acidified (pH-2) with 6N HCl and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (100 mL), dried (Na2SO4) and concentrated to afford the desired product (3.8 g, 84%) as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b37513711534aa6b5ada8f794560f89
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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