Sodium Hydroxide → 6-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505780Notes

Reaction equation

HRID 505780 reaction equation
[CH:1]1([C:7]2[C:8]3[S:20][C:19]([C:21]([O:23]C)=[O:22])=[CH:18][C:9]=3[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[CH:1]1([C:7]2[C:8]3[S:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][C:9]=3[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68467632methyl 6-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 113707856-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution (0.07 M) of methyl 6-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in THF/MeOH (1:1) was treated with aqueous NaOH (2 N solution, 15 eq.). The mixture was heated to reflux for 90 min then concentrated and acidified to pH 1 with aqueous HCl (6 N) and extracted with AcOEt. The combined organic phase was washed with brine then dried and concentrated to give the title compound (93%) as a solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 90 min
  3. concentrationthen concentrated
  4. extractionextracted with AcOEt
  5. washThe combined organic phase was washed with brine
  6. customthen dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0cb323c0709b46a89466f1c82410e381
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

Loading…