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

HRID 2393635Notes

Reaction equation

HRID 2393635 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].B.CO.O>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

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6331BoraneHCID 11048119HCID 11048119, compound

Product 1

HCID 11112334ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 350 g of (Z)-3-ethoxycarbonyl-4-(4-chloro phenyl)-4-(4-methanesulfonylphenyl)-3-butenoic acid, prepared in Example 63, in 1.5 l of tetrahydrofuran are added dropwise, and with good stirring, 120 ml of borane/dimethyl sulfide complex. At the end of the addition, the solution is stirred for 2.5 hours at room temperature. The borane in excess is hydrolyzed with 100 ml of methanol and 100 ml of water. After evaporation of the solvent under vacuum, the residue is crystallized in water, filtered and washed with water to give ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoate in the form of moist crystals which are used as such in the next step. By drying these crystals and recrystallizing them in propan-2-ol, ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoate is obtained in the form of crystals of HPLC purity 98.3% and of melting point 128° C.

Workup

  1. additionare added dropwise
  2. additionAt the end of the addition
  3. customAfter evaporation of the solvent under vacuum
  4. customthe residue is crystallized in water
  5. filtrationfiltered
  6. washwashed with water

Sources & evidence

ORD record
ord-313e31b4e2674da6b0d46edaa2bfd9f3
Source dataset
uspto-grants-1998_09
Patent number
US05807873

Reaction notes

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