Reaction #2161240

Reaction equation

hydrochloric acid

(4-hydroxyphenyl)diphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate

Methacryloyl chloride

triethylamine

→

(4-methacryloyloxyphenyl)diphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherprepared in Synthesis Example 45
2. 2
   Temperaturewas cooled in an ice bath
3. 3
   Otherafter which the organic layer was separated
4. 4
   Washwashed with 30 g of water three times
5. 5
   Concentrationconcentrated
6. 6
   OtherThe concentrate was purified by silica gel column chromatography (elute: dichloromethane/methanol 20/1 in weight ratio)
7. 7
   workup.ADDITIONafter which diethyl ether was added to the
8. 8
   Concentrationconcentrate for crystallization
9. 9
   FiltrationThe crystals were filtered
10. 10
    Otherdried
11. 11
    Otherobtaining the target compound in an amount of 3.5 g

Procedure

In 15 g of dichloromethane was dissolved 3 g of (4-hydroxyphenyl)diphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate (PAG29) prepared in Synthesis Example 45. Methacryloyl chloride, 1 g, was added to the solution, which was cooled in an ice bath, and 0.9 ml of triethylamine was added dropwise. 30 g of 3N dilute hydrochloric acid was added, after which the organic layer was separated, washed with 30 g of water three times, and concentrated. The concentrate was purified by silica gel column chromatography (elute: dichloromethane/methanol 20/1 in weight ratio), after which diethyl ether was added to the concentrate for crystallization. The crystals were filtered and dried, obtaining the target compound in an amount of 3.5 g.

Source