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Trifluoroacetic acid → HCID 13109064, Verbindung

HRID 1462975
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1462975
[CH2:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([OH:16])=[C:9]([O:14][CH3:15])[CH:10]=2)[CH:5]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[CH:2]=[CH2:3].FC(F)(F)C(O)=O>O=[V].Cl.Cl.Cl.C(Cl)Cl>[CH2:1]([N:4]1[CH:5]2[C:6]3=[C:7]([C:8]([OH:16])=[C:9]([O:14][CH3:15])[CH:10]=[C:11]3[CH2:12][CH2:13]1)[C:23]1[CH:22]=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1[CH2:17]2)[CH:2]=[CH2:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 13109061HCID 13109061, Verbindung

Produkt 1

HCID 13109064HCID 13109064, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24410Vanadium trichloride oxideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

22 g. (59.54 mmol) (+)-2-Allyl-7-hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline in a mixture of 190 ml. trifluoroacetic acid and 190 ml. anhydrous methylene chloride are mixed at -10° C., with the exclusion of moisture, with a solution of 6.0 ml. (11.04 g., 63.7 mmol) vanadium oxytrichloride in 190 ml. anhydrous methylene chloride. The reaction mixture is stirred for 30 minutes at -10° C., for 1 hour at 0° C. and for 2 hours at ambient temperature. Thereafter, the reaction mixture is concentrated to about one third of its volume by evaporation of the solvent in a vacuum at ambient temperature. The residue is mixed with ice water and extracted with chloroform. The chloroform phase is rendered basic with an aqueous solution of ammonia and worked up in the usual manner. By crystallisation from ethanol, there is obtained (+)-6-allyl-5,6,6a,7-tetrahydro-1-hydroxy-2,9,10-trimethoxy-4H-dibenzo(de,g)quinoline; m.p. 85°-93° C./134°-138° C.

Aufarbeitung

  1. concentrationThereafter, the reaction mixture is concentrated to about one third of its volume by evaporation of the solvent in a vacuum at ambient temperature
  2. additionThe residue is mixed with ice water
  3. extractionextracted with chloroform
  4. customBy crystallisation from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d32b274d02964fb980a0976183d621ff
Quelldatensatz
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04461895

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