Reaktion #511515

Reaktionsgleichung

hydrochloric acid

3-methacryloyloxyadamantane-carbonyl chloride

triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonate

triethylamine

→

triphenylsulfonium 1,1-difluoro-2-(3-methacryloyloxy-adamantane-1-carbonyloxy)-ethane-1-sulfonate

Ausbeute 82.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at a temperature below 5° C.
2. 2
   Waschenwashed with water, from which methylene chloride
3. 3
   workup.DISTILLATIONwas distilled off in vacuum
4. 4
   workup.ADDITION30 g of methyl isobutyl ketone was added to the residue, from which the residual water
5. 5
   workup.DISTILLATIONwas distilled off in vacuum together with methyl isobutyl ketone
6. 6
   workup.ADDITIONDiethyl ether was added to the residue for recrystallization
7. 7
   SonstigeThe resulting crystals were recovered
8. 8
   Sonstigedried

Vorschrift

To 3.3 g (11 mmol) of the 3-methacryloyloxyadamantane-carbonyl chloride were added 4.2 g (10 mmol) of triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonate in Synthesis Example 1-13 and 20 g of methylene chloride. To the mixture under ice cooling, a solution containing 1.1 g (11 mmol) of triethylamine and 0.25 g (2 mmol) of N,N-dimethylaminopyridine in 5 g of methylene chloride was added at a temperature below 5° C., and the resulting mixture was stirred for 2 hours at room temperature. Thereafter, 11 g of 5% dilute hydrochloric acid was added to the reaction mixture. The organic layer was taken out and washed with water, from which methylene chloride was distilled off in vacuum. 30 g of methyl isobutyl ketone was added to the residue, from which the residual water was distilled off in vacuum together with methyl isobutyl ketone. Diethyl ether was added to the residue for recrystallization. The resulting crystals were recovered and dried, obtaining the target compound, triphenylsulfonium 1,1-difluoro-2-(3-methacryloyloxy-adamantane-1-carbonyloxy)-ethane-1-sulfonate. White crystals, 5.5 g (yield 82%). The compound has the following structure.

Quelle