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Phosphoric Acid → methyl 6-benzyl-4-cyclohex-1-en-1-yl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate

HRID 505825
Notes
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Reaction equation

HRID 505825 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]2[CH:19]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[S:21][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.[C:33]1(=O)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.P(=O)(O)(O)O>C(O)(=O)C>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)[C:10]2[CH:19]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[S:21][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 7967CyclohexanoneHCID 68471240methyl 6-benzyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate

Product 1

HCID 68467568methyl 6-benzyl-4-cyclohex-1-en-1-yl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution (0.2 M) of methyl 6-benzyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate in acetic acid was treated with acetic anhydride (10 eq.), cyclohexanone (10 eq.) and 85% phosphoric acid (2.3 eq.). The mixture was heated at 80° C. for 3 h, then was poured into ice cold ammonium hydroxide. The product was extracted with AcOEt and the combined organic phase was washed sequentially with aqueous HCl (1 N), aqueous NaHCO3 (saturated solution) and brine then dried and concentrated. The crude was purified by flash chromatography on silica gel (1:30 acetone/toluene) affording the title compound (95%) as a solid.

Workup

  1. additionwas poured into ice cold ammonium hydroxide
  2. extractionThe product was extracted with AcOEt
  3. washthe combined organic phase was washed sequentially with aqueous HCl (1 N), aqueous NaHCO3 (saturated solution) and brine
  4. customthen dried
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography on silica gel (1:30 acetone/toluene)

Sources & evidence

ORD record
ord-95b360f9a3c646b79a7df11c424211a8
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07781431B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes