Triphenylsulfonium chloride → HCID 86642236, compound

HRID 1943568Notes

Reaction equation

HRID 1943568 reaction equation
[K].[C:2]([O:7][CH2:8][CH2:9][CH2:10][S:11]([OH:14])(=[O:13])=[O:12])(=[O:6])[C:3]([CH3:5])=[CH2:4].[Cl-].[C:16]1([S+:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[C:2]([O:7][CH2:8][CH2:9][CH2:10][S:11]([O-:14])(=[O:12])=[O:13])(=[O:6])[C:3]([CH3:5])=[CH2:4].[C:29]1([S+:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 61343Triphenylsulfonium chlorideHCID 1591573-[(2-Methylprop-2-enoyl)oxy]propane-1-sulfonic acidHCID 5462222Potassium

Product 1

HCID 86642236HCID 86642236, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 100 g of methylene chloride were added 2.5 g (10 mmol) of a potassium salt of 3-sulfopropyl methacrylate and 23 g (10 mmol) of an aqueous solution of triphenylsulfonium chloride prepared in Synthesis Example 1-1. The mixture was stirred at room temperature for 30 minutes. The organic layer was taken out and washed with water. It was combined with ethanol and concentrated in vacuum while azeotroping off the residual water. There was obtained 3.3 g of triphenylsulfonium 3-methacryloyloxypropanesulfonate. To 3.3 g of triphenylsulfonium 3-methacryloyloxypropanesulfonate were added 100 mg (0.6 mmol) of 28 wt % sodium methoxide in methanol and 15 g of methanol. The mixture was stirred at room temperature for 3 days. Then 70 mg of 35% aqueous hydrochloric acid was added to quench the reaction. The reaction solution was combined with methyl isobutyl ketone and concentrated in vacuum while distilling off the residual water. Diisopropyl ether was added to the residue for recrystallization. The crystals were collected and dried, obtaining the target compound, triphenylsulfonium 3-hydroxypropanesulfonate. White crystals, 2.1 g, yield 52%. The compound, designated PAG intermediate 2, has the following structure.

Workup

  1. customprepared in Synthesis Example 1-1
  2. washwashed with water
  3. concentrationconcentrated in vacuum
  4. customwhile azeotroping off the residual water

Sources & evidence

ORD record
ord-58cb5b78c925467d9c0c69ea21de72d2
Source dataset
uspto-grants-2013_03
Patent number
US08394570B2

Reaction notes

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