Triethylamine → Triphenylsulfonium 2-(adamantane-1-carbonyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate

HRID 2061312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061312
[F:1][C:2]([F:15])([F:14])[C:3]([OH:13])([C:9]([F:12])([F:11])[F:10])[CH2:4][S:5]([O-:8])(=[O:7])=[O:6].[C:16]1([S+:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.[C:42]12([C:52](Cl)=[O:53])[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:50][CH:44]([CH2:45]3)[CH2:43]1)[CH2:49]2>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:42]12([C:52]([O:13][C:3]([C:2]([F:1])([F:14])[F:15])([C:9]([F:12])([F:10])[F:11])[CH2:4][S:5]([O-:8])(=[O:7])=[O:6])=[O:53])[CH2:49][CH:48]3[CH2:47][CH:46]([CH2:45][CH:44]([CH2:50]3)[CH2:43]1)[CH2:51]2.[C:29]1([S+:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 86644254Triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate

Produkt 1

HCID 86644255Triphenylsulfonium 2-(adamantane-1-carbonyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Into a mixture solution of 5.2 g (10 mmoles) of triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate prepared in Synthesis Example 1-9, 1.1 g (11 mmoles) of triethylamine, 0.24 g (2 mmoles) of 4-dimethylaminopyridine, and 21 g of methylene chloride was added 5.5 g (11 mmoles) of a methylene chloride solution of adamantane-1-carbonyl chloride (40% by weight), and they were stirred at room temperature for 2 hours. Thereafter, the reaction was terminated by adding 12 g of 5% hydrochloric acid, and then the organic layer was separated, washed by water, and concentrated under reduced pressure. Into the concentrated solution was added methyl isobutyl ketone, and the resulted mixture was concentrated again under reduced pressure to distil the remaining water out. The obtained residue was washed by diisopropyl ether, and then dried to obtain the intended triphenylsulfonium 2-(adamantane-1-carbonyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate (2.7 g of oily substance (yield 39%)). The structure of the intended product is shown below.

Aufarbeitung

  1. customThereafter, the reaction was terminated
  2. additionby adding 12 g of 5% hydrochloric acid
  3. customthe organic layer was separated
  4. washwashed by water
  5. concentrationconcentrated under reduced pressure
  6. additionInto the concentrated solution was added methyl isobutyl ketone
  7. concentrationthe resulted mixture was concentrated again under reduced pressure
  8. customto distil the remaining water out
  9. washThe obtained residue was washed by diisopropyl ether
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3d827d9689634be8b98812b14d54265a
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283104B2

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