p-Toluenesulfonic acid monohydrate → Methyl 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetate

HRID 1085492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1085492
[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([CH2:13][C:14]([OH:16])=[O:15])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]2[CH:17]=[CH:18][S:19][C:3]1=2.O.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([CH2:13][C:14]([O:16][CH3:21])=[O:15])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]2[CH:17]=[CH:18][S:19][C:3]1=2

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 123447152-(10-oxo-4H-thieno[3,2-c][1]benzoxepin-8-yl)acetic acid

Produkt 1

HCID 13051081Methyl 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4,10-Dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetic acid, 25.5 g, synthesized according to the method of D.E. Aultz, et al. [J. Med. Chem., 20, 456 (1977)] and 0.9 g of p-toluenesulfonic acid monohydrate were heated under reflux for 3 hours in 600 ml of methanol. The solvent was distilled off under reduced pressure and the resulting residue was extracted with 500 ml of ethyl acetate. After washing in sequence with saturated sodium bicarbonate aqueous solution and then with saturated sodium chloride aqueous solution, the extract was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate= 3:1) to give 24.9 g of methyl 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetate as light yellow solids.

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionthe resulting residue was extracted with 500 ml of ethyl acetate
  3. washAfter washing in sequence with saturated sodium bicarbonate aqueous solution
  4. dry with materialwith saturated sodium chloride aqueous solution, the extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate= 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-db176ebba251477dbb6982a865b8bde7
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05010087

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