Hydrochloric Acid → HCID 22666364, compound

HRID 1007949Notes

Reaction equation

HRID 1007949 reaction equation
C(O[C:4]([C:6]1[CH:11]=[C:10]([F:12])[C:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([F:19])[C:7]=1F)=[O:5])C.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].CC(C)([O-])C.[K+].Cl.C[S:44](C)=O>C(OCC)(=O)C.O>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][C:9]1[C:10]([F:12])=[CH:11][C:6]2[C:4](=[O:5])[CH:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[S:44][C:7]=2[C:8]=1[F:19])[CH3:18]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 22666446HCID 22666446, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22666364HCID 22666364, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

In 66 mL of dimethyl sulfoxide is dissolved 15.2 g of ethyl 4-ethoxycarbonyl-2,3,6-trifluorophenylacetate, to which are added 7.84 g of potassium carbonate and 4.54 g of sodium hydrosulfide n-hydrate(purity 70%). The mixture is stirred at 40° C. for 2 hours. The reaction mixture is cooled to 5° C., 8.1 mL of tert-butyl chloroacetate is added, and the mixture thus formed is stirred at the same temperature as above for 20 minutes. Then, 6.36 g of potassium tert-butoxide is added and stirred for one hour. Water and ethyl acetate are added to the reaction mixture, pH is adjusted to 1 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water, saturated aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 19.2 g of tert-butyl 6-(2-ethoxy-2-oxoethyl)-5,7-difluoro-3-oxo-2,3-dihydrobenzo[b]thiophene-2-carboxylate is obtained.

Workup

  1. temperatureThe reaction mixture is cooled to 5° C.
  2. customthe mixture thus formed
  3. stirringis stirred at the same temperature as above for 20 minutes
  4. stirringstirred for one hour
  5. customthe organic layer is separated
  6. washThe organic layer is washed with water, saturated aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-d1b3616d65464b2fa6ce0761c6c8ae85
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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