Ethylene Glycol → HCID 68470999, compound

HRID 505799Notes

Reaction equation

HRID 505799 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[C:13]([CH:20]=[O:21])=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:10]=3[C:9]=2[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:4][CH:3]=1.[CH2:28]([OH:31])[CH2:29]O.[CH3:32]C1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:32])[C:11]3[C:13]([CH:20]4[O:31][CH2:28][CH2:29][O:21]4)=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:10]=3[C:9]=2[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 86627061HCID 86627061, compound

Product 1

HCID 68470999HCID 68470999, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution (0.15 M) of methyl 5-(4-chlorophenyl)-6-cyclohexyl-3-formyl-4H-thieno[3,2-b]pyrrole-2-carboxylate, ethylene glycol (10 eq.) and a catalytic amount of p-TsOH in toluene was refluxed (Dean-Stark) for 3 h. After cooling down to RT solid NaHCO3 was added and the mixture was diluted with AcOEt and water. The layers were separated and the aqueous layer was extracted with AcOEt. The combined organic phase was dried. Evaporation of the solvent under reduced pressure afforded a residue that was purified by flash chromatography on silica gel (1:3 AcOEt/petroleum ether) to afford the title compound (89%) as a yellow solid.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with AcOEt
  4. customThe combined organic phase was dried
  5. customEvaporation of the solvent under reduced pressure
  6. customafforded a residue that
  7. customwas purified by flash chromatography on silica gel (1:3 AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-d1668f9202524113a93c946cf263cf74
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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