Potassium Carbonate → HCID 19347978, compound

HRID 1637190Notes

Reaction equation

HRID 1637190 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]2[CH:21]=[CH:20][C:19]([CH2:22][O:23]C(C)=O)=[CH:18][C:10]=2[S:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[Cl:7][C:8]1[C:9]2[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][C:10]=2[S:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19347981HCID 19347981, compound

Product 1

HCID 19347978HCID 19347978, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium carbonate (2 g) was added to a stirred solution of ethyl 3-chloro-6-[(methylcarbonyloxy)methyl]benzo[b]thiophene-2-carboxylate (Preparation 14, 2.65 g, 8.5 mmol) in ethanol (40 ml). The mixture was stirred at ambient temperature for 20 hours, then the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane and water. The organic layer was separated and washed with more water, dried (magnesium sulfate), and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using a gradient of 0-2% methanol in dichloromethane as eluant to give the title compound, which was crystallised from diethyl ether to give a colourless solid (1.66 g).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between dichloromethane and water
  3. customThe organic layer was separated
  4. washwashed with more water
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated under reduced pressure
  7. customchromatographed on silica gel using a gradient of 0-2% methanol in dichloromethane as eluant

Sources & evidence

ORD record
ord-5f2ac42ca9b844e19fd273a9edbda7df
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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