3,4-dihydro-2H-pyran → HCID 54008977, Verbindung

HRID 2295287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2295287
[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.CC1C=CC(S(O)(=O)=O)=CC=1.O.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 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 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 ptoluenesulfonic 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 etherhexane 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-4ef8cb3388ce4452a3396e5414b3a905
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04424213

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