Reaktionsgleichung
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]3[NH:15][CH:16]=[C:17]([CH2:18][CH2:19][OH:20])[C:11]=3[CH:10]=2)=[CH:3][CH:2]=1.[C:21]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:22][C:23]([CH3:25])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:25][C:23]1([CH2:22][C:21]([O:27][CH2:28][CH3:29])=[O:26])[C:16]2[NH:15][C:12]3[C:11]([C:17]=2[CH2:18][CH2:19][O:20]1)=[CH:10][C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[CH:14][CH:13]=3Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture consisting of 5-benzyloxytryptophol (4.5 g, 0.017 mol), benzene (200 mL), ethyl acetoacetate (3.4 g, 0.026 mol) and p-toluenesulfonic acid (0.5 g) is refluxed for 2.5 hours using a Dean-stock trap to remove the water. The reaction mixture is cooled to room temperature and washed with 5% sodium bicarbonate, (1×200 mL), water (200 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated to give 8.0 g of crude product as a thick oil, which is flash chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent to afford 5.5 g oil which solidifies upon standing, m.p. 96°-98° C.
Aufarbeitung
- temperatureis refluxed for 2.5 hours
- customto remove the water
- washwashed with 5% sodium bicarbonate, (1×200 mL), water (200 mL) and brine (100 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customto give 8.0 g of crude product as a thick oil, which
- customchromatographed on silica gel using 20% ethyl acetate/hexane as an eluent
Quellen und Nachweise
- ORD-Eintrag
- ord-81281567c4c44990919e4c9f2a565b1f
- Quelldatensatz
- uspto-grants-1993_07
- Patentnummer
- US05229516
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