Methanol → ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoate

HRID 1740828Notes

Reaction equation

HRID 1740828 reaction equation
[CH2:1]([O:3][C:4](/[C:6](=[C:11](\[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][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>[Cl:28][C:25]1[CH:24]=[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]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 11048119HCID 11048119, compound

Product 1

HCID 11112334ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoateYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 32.8 g (0.0775 mole) of (Z)-3-ethoxycarbonyl-4-(4-chlorophenyl)-4-(4-methanesulphonylphenyl)but-3-enoic acid, prepared in example 3, in 90 ml of anhydrous tetrahydrofuran are added dropwise 15.5 ml (0.155 mole) of borane/dimethyl sulphide complex. 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 in vacuo and the residue is dissolved in ethyl acetate. After washing with potassium carbonate solution, the organic phase is separated, dried over magnesium sulphate and evaporated in vacuo to give 30.8 g of ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulphonylphenyl)-2-(2-hydroxyethyl)prop-2-enoate as crystals with a melting point of 128° C. after recrystallisation from isopropanol.

Workup

  1. additionare added dropwise 15.5 ml (0.155 mole) of borane/dimethyl sulphide complex
  2. customThe mixture is evaporated to dryness in vacuo
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washAfter washing with potassium carbonate solution
  5. customthe organic phase is separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-eca2e9df6c004bd4ba227870ba264d1f
Source dataset
uspto-grants-1999_10
Patent number
US05972950

Reaction notes

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