Triethylamine → Bis(4-tert-butylphenyl)iodonium 2-(adamantane-1-carbonyloxy)ethanesulfonate

HRID 1943571

Reaktionsgleichung

Reaktionsgleichung von HRID 1943571
[S:1]([CH2:5][CH2:6][OH:7])([O-:4])(=[O:3])=[O:2].[Na+].C(N(CC)CC)C.[C:16]12([C:26](Cl)=[O:27])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.S([O-])(O)(=O)=O.[C:34]([C:38]1[CH:43]=[CH:42][C:41]([I+:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:47][CH:46]=2)=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35]>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C)C1C=CN=CC=1.ClCCl.C(C(C)=O)C(C)C>[C:16]12([C:26]([O:7][CH2:6][CH2:5][S:1]([O-:4])(=[O:3])=[O:2])=[O:27])[CH2:23][CH:22]3[CH2:21][CH:20]([CH2:19][CH:18]([CH2:24]3)[CH2:17]1)[CH2:25]2.[C:51]([C:48]1[CH:49]=[CH:50][C:45]([I+:44][C:41]2[CH:40]=[CH:39][C:38]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:43][CH:42]=2)=[CH:46][CH:47]=1)([CH3:54])([CH3:53])[CH3:52]

Komponenten

10

Edukt 4

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 517063Sodium IsethionateHCID 20205689Bis(4-tert-butylphenyl)iodanium hydrogen sulfate

Produkt 1

HCID 86642239Bis(4-tert-butylphenyl)iodonium 2-(adamantane-1-carbonyloxy)ethanesulfonateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

In water, 5.1 g (0.035 mole) of sodium isethionate and 6.4 g (0.053 mole) of benzyltrimethylammonium chloride were mixed and dissolved. The solution was concentrated by removing water in vacuum. The concentrate was dispersed in 55 g of acetonitrile. To the dispersion, 5.2 g (0.052 mole) of triethylamine and 0.42 g (0.0035 mole) of 4-(dimethylamino)pyridine were added, and under ice cooling, 20.6 g (0.052 mole) of 50% adamantane-1-carbonyl chloride in dichloromethane was then added dropwise. The reaction mixture was stirred at room temperature over night. Water was added to quench the reaction, from which acetonitrile was distilled off in vacuum. An amount (0.0088 mole) of bis(4-tert-butylphenyl)iodonium hydrogensulfate prepared in Synthesis Example 1-6 and 50 g of methyl isobutyl ketone were added to the residue, followed by stirring at room temperature for 1 hour. The organic layer was taken out, washed with water, and concentrated in vacuum. Diisopropyl ether was added to the concentrate for recrystallization. The crystals were collected and dried, obtaining the target compound, bis(4-tert-butylphenyl)iodonium 2-(adamantane-1-carbonyloxy)ethanesulfonate. White crystals, 5.7 g, yield 95%. The compound, designated PAG-6, has the following structure.

Aufarbeitung

  1. dissolutiondissolved
  2. concentrationThe solution was concentrated
  3. customby removing water in vacuum
  4. additionThe concentrate was dispersed in 55 g of acetonitrile
  5. customto quench
  6. customthe reaction
  7. distillationfrom which acetonitrile was distilled off in vacuum
  8. additionwere added to the residue
  9. stirringby stirring at room temperature for 1 hour
  10. washwashed with water
  11. concentrationconcentrated in vacuum
  12. additionDiisopropyl ether was added to the
  13. concentrationconcentrate for recrystallization
  14. customThe crystals were collected
  15. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f071d8395b884546968fc8bf3741de5f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394570B2

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