Ethanol → HCID 17989196, compound

HRID 1443300Notes

Reaction equation

HRID 1443300 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])=[C:4]([O:17][CH3:18])[C:3]=1[F:19].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:30](O)[CH3:31]>>[CH2:30]([O:12][C:11](=[O:13])[C:10](=[O:14])[CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:19])[C:4]=1[O:17][CH3:18])([CH3:16])[CH3:15])[CH3:31]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 17989224HCID 17989224, compound

Product 1

HCID 17989196HCID 17989196, compound

Procedure

5.44 g (18.84 mmol) of 4-(4-chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-oxo-pentanoic acid is dissolved in 117 ml of ethanol, mixed with 2.1 ml of concentrated sulfuric acid, and refluxed for six hours. The reaction mixture is added to 250 ml of saturated sodium bicarbonate solution, and extracted three times with ethyl acetate. The combined organic extracts are washed with saturated sodium bicarbonate solution and with brine. After drying, and after the dessicant is filtered off and the solvent is spun in, 5.19 g (87%) of the desired compound is obtained.

Workup

  1. temperaturerefluxed for six hours
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic extracts are washed with saturated sodium bicarbonate solution and with brine
  4. customAfter drying
  5. filtrationafter the dessicant is filtered off
  6. customis obtained

Sources & evidence

ORD record
ord-bf6ed549aee44a15a932cf1fc110ab73
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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