Hydrochloric Acid → HCID 70194376, compound

HRID 568074Notes

Reaction equation

HRID 568074 reaction equation
[Cl-].[Ca+2].[Cl-].C(O[C:7]([C:9](=[C:14]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1)[CH2:10][C:11]([OH:13])=[O:12])=O)C.[BH4-].[Na+].[OH-].[K+].Cl>C(O)C.O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:14](=[C:9]2[CH2:7][O:13][C:11](=[O:12])[CH2:10]2)[C:15]2[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:19][CH:20]=2)=[CH:26][CH:27]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 53824172HCID 53824172, compound

Product 1

HCID 70194376HCID 70194376, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

13.6 g of powdered anhydrous calcium chloride are added to a solution of 3-ethoxycarbonyl-4-(4-fluorophenyl)-4-(4-methanesulphonylphenyl)-3-butenoic acid, prepared in Example 43, in 500 ml of ethanol. The mixture is stirred at room temperature and a solution of 7.5 g of sodium borohydride in a mixture composed of 1.5 g of potassium hydroxide, 10 ml of water and 10 ml of ethanol is added dropwise while cooling with an ice bath. After 4 hours at room temperature, the reaction medium is cooled to 0° C. and 6 N hydrochloric acid solution is added dropwise. After extraction with dichloromethane, the organic phase is dried over magnesium sulphate and evaporated under vacuum and the residue is crystallised from isopropyl ether. The crystals obtained are recrystallized from methanol to give 5 g of 4-[1-(4-fluorophenyl)-1-(4-methanesulphonylphenyl)methylidene]-dihydrofuran-2-one in the form of a mixture (50/50) of the two isomers, (E) and (Z), which are crystals melting at 160-164° C.

Workup

  1. additionis added dropwise
  2. temperaturewhile cooling with an ice bath
  3. temperaturethe reaction medium is cooled to 0° C.
  4. extractionAfter extraction with dichloromethane
  5. dry with materialthe organic phase is dried over magnesium sulphate
  6. customevaporated under vacuum
  7. customthe residue is crystallised from isopropyl ether
  8. customThe crystals obtained
  9. customare recrystallized from methanol

Sources & evidence

ORD record
ord-544fd91a83fb4ed583e6aa6a54760284
Source dataset
uspto-grants-2001_01
Patent number
US06180651B2

Reaction notes

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