4-Toluenesulfonyl chloride → Z-1-(4-methylphenylsulfonyloxymethyl)-1-(4-fluorophenyl)-2-(3-cyclohexenyl)-ethene

HRID 1613619Notes

Reaction equation

HRID 1613619 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:12][CH2:13]/[C:14](/[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[CH:15]\[CH:16]1[CH2:21][CH2:20][CH:19]=[CH:18][CH2:17]1>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:12][CH2:13]/[C:14](/[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:15]\[CH:16]2[CH2:21][CH2:20][CH:19]=[CH:18][CH2:17]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19774242Z-1-hydroxymethyl-1-(4-fluorophenyl)-2-(3-cyclohexenyl)ethene

Product 1

HCID 86745997Z-1-(4-methylphenylsulfonyloxymethyl)-1-(4-fluorophenyl)-2-(3-cyclohexenyl)-etheneYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

32.5 g of 4-methylbenzenesulfonyl chloride are added, at room temperature, to a solution of 34 g of Z-1-hydroxymethyl-1-(4-fluorophenyl)-2-(3-cyclohexenyl)ethene in 200 ml of methylene chloride and 29 g of triethylamine. After 24 hours, the reaction mixture is washed with aqueous sodium bicarbonate solution and water, dried over sodium sulfate and evaporated down under reduced pressure. 49.7 g (95%) of Z-1-(4-methylphenylsulfonyloxymethyl)-1-(4-fluorophenyl)-2-(3-cyclohexenyl)-ethene are obtained from the residue.

Workup

  1. washthe reaction mixture is washed with aqueous sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-04b1428a8e11497097d68969c217de66
Source dataset
uspto-grants-1993_03
Patent number
US05194444

Reaction notes

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