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

HRID 1951647Notes

Reaction equation

HRID 1951647 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][CH:6]=1)=[O:4].CO.O.[Li+].[OH-]>C1COCC1.CC(O)=O>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]2[CH:11]=[CH:12][C:8]3[S:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:9]2=3)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67182634HCID 67182634, compound

Product 1

HCID 671836564-(4-Trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole-3-carboxylic acidYield 93.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.0 g of the product of Step 6 was dissolved in 45 ml THF, 30 ml of MeOH and 15 ml of water, followed by 15 ml of 1N aqueous LiOH solution. After stirring for 5 h at room temperature, 2 ml of AcOH was added and the mixture was extracted with 150 ml of EtOAc. The organic layer was washed with 50 ml of brine and dried over Na2SO4, filtered, and concentrated to give 0.9 g of the title compound as a white solid.

Workup

  1. extractionthe mixture was extracted with 150 ml of EtOAc
  2. washThe organic layer was washed with 50 ml of brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1fe8d0f33ae5477189a9f323fa700212
Source dataset
uspto-grants-2013_03
Patent number
US08404736B2

Reaction notes

Loading…