Methanol → HCID 54386099, compound

HRID 568071Notes

Reaction equation

HRID 568071 reaction equation
[CH2:1]([O:3][C:4]([C:6](=[C:11]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:7][C:8](O)=[O:9])=[O:5])[CH3:2].CO>O1CCCC1>[F:28][C:24]1[CH:23]=[C:22]([C:11]([C:12]2[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][CH:17]=2)=[C:6]([CH2:7][CH2:8][OH:9])[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 54478229HCID 54478229, compound

Product 1

HCID 54386099HCID 54386099, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.5 ml (0.155 mol) of borane/methyl sulphide complex are added dropwise to a solution of 31.5 g (0.0775 mol) of 3-ethoxycarbonyl-4-(3-fluorophenyl)-4-(4-methanesulphonylphenyl)-3-butenoic acid, prepared in Example 11, in 90 ml of anhydrous tetrahydrofuran. The mixture is stirred at room temperature for 8 hours and 23.5 ml of methanol are added dropwise. The mixture is evaporated to dryness under vacuum and the residue is taken up with ethyl acetate and then treated with an aqueous solution of 7.6 g of potassium carbonate. The organic phase is decanted and then dried over magnesium sulphate and evaporated to dryness under vacuum to give 29.3 g of ethyl 3-(3-fluorophenyl)-3-(4-methanesulphonylphenyl)-2-(2-hydroxyethyl)-2-propenoate in the form of a viscous oil, which is used as such in the next step.

Workup

  1. customThe mixture is evaporated to dryness under vacuum
  2. additiontreated with an aqueous solution of 7.6 g of potassium carbonate
  3. customThe organic phase is decanted
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-8ee6ae842bd14c4bbcf21b3aeef8c5fa
Source dataset
uspto-grants-2001_01
Patent number
US06180651B2

Reaction notes

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