Ethyl Acetate → HCID 86627061, compound

HRID 505798Notes

Reaction equation

HRID 505798 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](COC)[C:11]3[C:16]([CH:23]=[O:24])=[C:17]([C:19]([O:21][CH3:22])=[O:20])[S:18][C:10]=3[C:9]=2[CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:4][CH:3]=1.CCOC(C)=O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]3[C:16]([CH:23]=[O:24])=[C:17]([C:19]([O:21][CH3:22])=[O:20])[S:18][C:10]=3[C:9]=2[CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86627060HCID 86627060, compound

Product 1

HCID 86627061HCID 86627061, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution (0.11 M) of methyl 5-(4-chlorophenyl)-6-cyclohexyl-3-formyl-4-(methoxymethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in dioxane/aqueous HCl (6 N) (1:1) was heated at 130° C. under microwave irradiation for 10 min. After dilution with AcOEt, the resulting solution was basified with solid NaHCO8 and extracted with AcOEt. The combined organic phase was washed with brine, dried and concentrated under reduced pressure. The crude was triturated with Et2O/petroleum ether (1:9) to afford the title compound (70%) as a solid.

Workup

  1. extractionextracted with AcOEt
  2. washThe combined organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was triturated with Et2O/petroleum ether (1:9)

Sources & evidence

ORD record
ord-92ab23a20e5f43e3ae46e09bfab63095
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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