Dimethyl Sulfoxide → 2,3,4,5-Tetrahydro-1-benzoxepin-6-carboxaldehyde

HRID 342082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342082
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=O.[O:11]1[C:17]2[CH:18]=[CH:19][CH:20]=C[C:16]=2[CH2:15][CH:14](CO)[CH2:13][CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]1[C:17]2=[CH:18][CH:19]=[CH:20][C:6]([CH:5]=[O:9])=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18787485HCID 18787485, Verbindung

Produkt 1

HCID 187873792,3,4,5-Tetrahydro-1-benzoxepin-6-carboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

DMSO (1.85 ml, 26 mmol) was added slowly to a -78° C. solution of oxalyl chloride in methylene chloride (10 ml of 2M, 20 mmol). To this solution was added slowly a solution of 2,3,4,5-tetrahydrobenzoxepin-4-methanol (2.3 g, 13 mmol) in methylene chloride, and the mixture was stirred 30 min at -78° C. Triethyl amine (7.53 ml, 52 mmol) was added slowly to the reaction mixture, which was then allowed to warm to room temperature. The mixture was diluted with methylene chloride (50 ml) and washed with water and then brine. The organic layer was concentrated in vacuo to an oil (2.28 g, 100%).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. concentrationThe organic layer was concentrated in vacuo to an oil (2.28 g, 100%)

Quellen und Nachweise

ORD-Eintrag
ord-568d8fab32a94863b58c8e14890a3325
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856529

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