p-Toluenesulfonic acid → HCID 54008977, Verbindung

HRID 464641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464641
[CH:1]12[CH2:8][CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[N:9][OH:10])[S:2]2.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:10][N:9]=[C:3]1[CH:4]2[CH2:7][CH2:8][CH:1]([CH:6]=[CH:5]2)[S:2]1

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 71415470N-2-Thiabicyclo[2.2.2]oct-5-en-3-ylidenehydroxylamine

Produkt 1

HCID 54008977HCID 54008977, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 10 g (0.06 m) of 2-thiabicyclo[2.2.2]oct-5-en-3-one oxime, 9 g (0.1 m) of 98% dihydropyran, and a catalytic amount of p-toluenesulfonic acid in 30 ml of methylene chloride was heated under reflux overnight. Sodium bicarbonate was added to neutrality. The residue after removal of solvent was purified by dry column chromatography (silica gel-ethyl acetate:hexane::1:1) to give 14.4 g of yellow solid. Recrystallization from ether-hexane yielded 10.1 g of the title compound as a white solid, m. 84°-5° C.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. customThe residue after removal of solvent
  3. customwas purified
  4. dry with materialby dry column chromatography (silica gel-ethyl acetate:hexane::1:1)

Quellen und Nachweise

ORD-Eintrag
ord-6fd33b4799be44808983ea32d19c9adb
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04548929

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