Ethylene Glycol → 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

HRID 46516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46516
[O:1]=[C:2]([CH3:22])[CH2:3][C:4]1[C:5](=[O:21])[NH:6][CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]=12.[CH2:23](O)[CH2:24][OH:25].B(F)(F)F.CCOCC.[OH-].[Na+]>C1C=CC=CC=1.O>[CH3:22][C:2]1([CH2:3][C:4]2[C:5](=[O:21])[NH:6][CH2:7][CH2:8][CH:9]3[CH2:18][CH2:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=4)[C:10]=23)[O:25][CH2:24][CH2:23][O:1]1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 128324091-(2-oxo-propyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Produkt 1

HCID 205556101-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

The starting material is prepared as follows: The mixture of 20 g of 1-(2-oxopropyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one, 37.5 ml of ethylene glycol and 0.95 g of boron trifluoride etherate in benzene is refluxed under a water trap for 6 hours. It is cooled and 10 g of sodium hydroxide in 140 ml of water are added rapidly and the mixture is extracted with chloroform. The extract is dried, evaporated and the residue is crystallized from diethyl ether, to yield the 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one melting at 192°-194°.

Aufarbeitung

  1. customThe starting material is prepared
  2. temperatureis refluxed under a water trap for 6 hours
  3. temperatureIt is cooled
  4. extractionthe mixture is extracted with chloroform
  5. customThe extract is dried
  6. customevaporated
  7. customthe residue is crystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a0a0e22347714b3aa0c04887ae6f819c
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173633

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