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Hydrochloric Acid → Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(3-methacryloyloxy-adamantane-1-carbonyloxy)-propane-1-sulfonate

HRID 556247
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Reaktionsgleichung von HRID 556247
[C:1]([O:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][C:9]([C:17](Cl)=[O:18])([CH2:10]3)[CH2:8]1)[CH2:14]2)(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:20][CH:21]([C:29]([F:32])([F:31])[F:30])[C:22]([F:28])([F:27])[S:23]([O-:26])(=[O:25])=[O:24].[C:33]1([S+:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[F:28][C:22]([F:27])([S:23]([O-:26])(=[O:24])=[O:25])[CH:21]([O:20][C:17]([C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:16][C:7]([O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])([CH2:14]3)[CH2:8]1)[CH2:10]2)=[O:18])[C:29]([F:30])([F:32])[F:31].[C:46]1([S+:39]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 86612198Triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropanesulfonateHCID 866395133-Methacryloyloxyadamantanecarbonyl chloride

Produkt 1

HCID 86639512Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(3-methacryloyloxy-adamantane-1-carbonyloxy)-propane-1-sulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturecooled
  2. customexceed 5° C.
  3. customThe organic layer was separated
  4. washwashed with water whereupon methylene chloride
  5. distillationwas distilled off under vacuum
  6. washwashed with dilute aqueous ammonia
  7. distillationwith water, whereupon the methyl isobutyl ketone was distilled off under vacuum
  8. additionDiisopropyl ether was added to the residue

Quellen und Nachweise

ORD-Eintrag
ord-69788b8d58864698b95c50371623e9e7
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08057985B2

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