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3-methacryloyloxyadamantanecarbonyl chloride

triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate

triethylamine

hydrochloric acid

→

triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(3-methacryloyloxy-adamantane-1-carbonyloxy)-propane-1-sulfonate

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   온도cooled
2. 2
   기타exceed 5° C.
3. 3
   기타The organic layer was separated
4. 4
   세척washed with water whereupon methylene chloride
5. 5
   workup.DISTILLATIONwas distilled off under vacuum
6. 6
   세척washed with dilute aqueous ammonia
7. 7
   workup.DISTILLATIONwith water, whereupon the methyl isobutyl ketone was distilled off under vacuum
8. 8
   workup.ADDITIONDiisopropyl ether was added to the residue

실험 절차

To 28.4 g (0.10 mole) of the resulting 3-methacryloyloxyadamantanecarbonyl chloride were added 44.9 g (0.09 mole) of triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate in Synthesis Example 1-11 and 20 g of methylene chloride, which was ice cooled. To the solution, a solution of 10.1 g (0.10 mole) of triethylamine and 2.2 g (0.02 mole) of N,N-dimethylaminopyridiene in 45 g of methylene chloride was added such that the temperature might not exceed 5° C., followed by stirring at room temperature for 7 hours. Thereafter, 105 g of 5% dilute hydrochloric acid was added. The organic layer was separated and washed with water whereupon methylene chloride was distilled off under vacuum. The residue was combined with 250 g of methyl isobutyl ketone and washed with dilute aqueous ammonia and then with water, whereupon the methyl isobutyl ketone was distilled off under vacuum. Diisopropyl ether was added to the residue, followed by decantation. The target compound, triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(3-methacryloyloxy-adamantane-1-carbonyloxy)-propane-1-sulfonate was obtained as brown oil (61.7 g, yield 92%). The compound has the following structure.

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