Hydrochloric Acid → HCID 54478229, compound

HRID 568070Notes

Reaction equation

HRID 568070 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1)=O.CC(C)([O-])C.[K+].[C:26]([O:33][CH2:34][CH3:35])(=[O:32])[CH2:27][CH2:28][C:29]([O-:31])=[O:30].Cl>C(O)(C)(C)C.O>[CH2:34]([O:33][C:26]([C:27](=[C:5]([C:4]1[CH:17]=[CH:18][CH:19]=[C:2]([F:1])[CH:3]=1)[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1)[CH2:28][C:29]([OH:31])=[O:30])=[O:32])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 17119674-Ethoxy-4-oxobutanoateHCID 21262864HCID 21262864, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54478229HCID 54478229, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

35.5 g (0.1275 mol) of 3-fluoro-4′-methanesulphonylbenzophenone, prepared in Example 10, are added in portions to a solution of 15.7 g (0.140 mol) of potassium t-butoxide in 100 ml of t-butanol. The mixture is stirred and 32 ml (0.191 mol) of ethyl succinate are added dropwise at a rapid rate. The mixture is subsequently refluxed for 30 minutes and cooled, water and 1 N hydrochloric acid are added to bring the pH to 1 and the mixture is then extracted with t-butyl methyl ether. The organic phase is treated with 2% sodium hydroxide solution and the mixture is decanted. The aqueous phase is acidified with 1 N hydrochloric acid and then extracted with t-butyl methyl ether. The organic phase is dried over magnesium sulphate and evaporated under vacuum to give 39.2 g of 3-ethoxycarbonyl-4-(3-fluorophenyl)-4-(4-methanesulphonylphenyl)-3-butenoic acid in the form of a thick oil, which is used as such in the next step.

Workup

  1. temperatureThe mixture is subsequently refluxed for 30 minutes
  2. temperaturecooled
  3. extractionthe mixture is then extracted with t-butyl methyl ether
  4. additionThe organic phase is treated with 2% sodium hydroxide solution
  5. customthe mixture is decanted
  6. extractionextracted with t-butyl methyl ether
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-8b4cc221d3a843b6839c5a774ed4ae03
Source dataset
uspto-grants-2001_01
Patent number
US06180651B2

Reaction notes

Loading…