Potassium Carbonate → HCID 86605564, compound

HRID 1819952Notes

Reaction equation

HRID 1819952 reaction equation
[CH2:1]([C:3]([C:14]1[S:18][C:17]([S:19]([OH:22])(=[O:21])=[O:20])=[C:16]([CH3:23])[CH:15]=1)([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH3:13])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>CC(=O)CC>[CH3:34][C:33]([CH3:36])([CH3:35])[C:32](=[O:37])[CH2:31][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:3]([C:14]2[S:18][C:17]([S:19]([OH:22])(=[O:21])=[O:20])=[C:16]([CH3:23])[CH:15]=2)([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][C:8]=1[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 835721-ChloropinacoloneHCID 86605563HCID 86605563, compound

Product 1

HCID 86605564HCID 86605564, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 5-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-3-methyl-thiophene-2-sulfonic acid dimethylaminemethyleneamide (5.1 g, 12.48 mmol) in 2-butanone (50 ml) is added potassium carbonate (2.59 g, 18.72 mmol), and chloropinacolone (3.28 ml, 24.91 mmol). The reaction is refluxed overnight, filtered, and concentrated. The residue is partitioned between EtOAc (400 ml) and 0.2N HCl (100 ml). The organic layer is washed with brine (100 ml), MgSO4 dried, concentrated, and chromatographed (120 g SiO2, 50% EtOAc/Hex) to yield the title compound (6.11 g, 97%).

Workup

  1. temperatureThe reaction is refluxed overnight
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue is partitioned between EtOAc (400 ml) and 0.2N HCl (100 ml)
  5. washThe organic layer is washed with brine (100 ml), MgSO4
  6. customdried
  7. concentrationconcentrated
  8. customchromatographed (120 g SiO2, 50% EtOAc/Hex)

Sources & evidence

ORD record
ord-312a0c4b33e7472b922c270c7d0d28b1
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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