반응 #511515

반응 방정식

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

수율 82.0%

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   workup.ADDITIONwas added at a temperature below 5° C.
2. 2
   세척washed 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
   기타The resulting crystals were recovered
8. 8
   기타dried

실험 절차

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.

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