Ethanol → (Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)-methylene]-1,4-butanediol

HRID 1740834Notes

Reaction equation

HRID 1740834 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[C:19](/[CH2:23][C:24](O)=[O:25])\[C:20](O)=[O:21])/[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(O)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](=[C:19](/[CH2:23][CH2:24][OH:25])\[CH2:20][OH:21])/[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 21833695(Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)methylene]succinic acid

Product 1

HCID 21833699(Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)-methylene]-1,4-butanediolYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7.85 g (0.0199 mole) of (Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)methylene]succinic acid, prepared in example 28, in 40 ml of tetrahydrofuran are added dropwise 5.65 ml (0.0596 mole) of borane/dimethyl sulphide complex. The mixture is then stirred for 3 hours at ambient temperature and then 1 hour at 50° C. After returning to ambient temperature, 5 ml of ethanol are added dropwise. The mixture is then concentrated to half its volume and then taken up into water. The crystals obtained are filtered off under suction and washed with pentane and dried giving 6.92 g of (Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)-methylene]-1,4-butanediol in the form of crystals with a melting point of 159-160° C.

Workup

  1. additionare added dropwise 5.65 ml (0.0596 mole) of borane/dimethyl sulphide complex
  2. custom1 hour
  3. customat 50° C
  4. customAfter returning to ambient temperature
  5. concentrationThe mixture is then concentrated to half its volume
  6. customThe crystals obtained
  7. filtrationare filtered off under suction
  8. washwashed with pentane
  9. customdried

Sources & evidence

ORD record
ord-b2728843c2a64069a005ff55673b204e
Source dataset
uspto-grants-1999_10
Patent number
US05972950

Reaction notes

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