Methanol → 2-Methyl-4-(4-(trifluoromethyl)benzyl)-4H-thieno[3,2-b]pyrrole-3-carboxylic acid

HRID 1951641Notes

Reaction equation

HRID 1951641 reaction equation
C[O:2][C:3]([C:5]1[C:9]2[N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[CH:12][C:8]=2[S:7][C:6]=1[CH3:24])=[O:4].CO.O.[Li+].[OH-]>C1COCC1.CC(O)=O>[CH3:24][C:6]1[S:7][C:8]2[CH:12]=[CH:11][N:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=3)[C:9]=2[C:5]=1[C:3]([OH:4])=[O:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 671837132-Methyl-4-(4-trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 671826242-Methyl-4-(4-(trifluoromethyl)benzyl)-4H-thieno[3,2-b]pyrrole-3-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.35 g of the product of Step 6 was dissolved in 15 ml THF, 10 ml of MeOH and 5 ml of water, followed by 5 ml of 1N aqueous LiOH solution. After stirring for 5 h at room temperature, 1 ml of AcOH was added and the mixture was extracted with 50 ml of EtOAc. The organic layer was washed with 25 ml of brine and dried over Na2SO4, filtered, and concentrated to give 0.30 g of the title compound as a white solid.

Workup

  1. extractionthe mixture was extracted with 50 ml of EtOAc
  2. washThe organic layer was washed with 25 ml of brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6a8b813d09e74d41963f0ac9615694e4
Source dataset
uspto-grants-2013_03
Patent number
US08404736B2

Reaction notes

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