Oxalic Acid → 1,10-Dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole-1-propionaldehyde

HRID 1833557

Reaktionsgleichung

Reaktionsgleichung von HRID 1833557
[CH3:1][C:2]1([CH2:16][CH2:17][CH2:18][OH:19])[C:7]2=[C:8]([CH3:15])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][O:3]1.FC(F)(F)C(O)=O.N1C=CC=CC=1.C(O)(=O)C(O)=O>O.CO.CCOCC>[CH3:1][C:2]1([CH2:16][CH2:17][CH:18]=[O:19])[C:7]2=[C:8]([CH3:15])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][O:3]1

Komponenten

8

Edukt 4

HCID 971Oxalic AcidHCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 213895531,10-Dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole-1-propanol

Produkt 1

HCID 213895661,10-Dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole-1-propionaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

N,N-Dicyclohexylcarbodiimide (2.87 g.) is added to a cooled, stirred solution of the primary alcohol, 1,10-dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole-1-propanol (1.0 g.), described in Example 462, in 10 ml. of dimethyl sulfoxidebenzene (2:1) containing trifluoroacetic acid (0.18 ml.) and pyridine (0.38 ml.). The reaction is stirred at room temperature under nitrogen for 5 hr. The reaction mixture is now diluted with 100 ml. of ether, followed by the dropwise addition of a solution of oxalic acid (1.26 g.) in 6 ml. of methanol. After thirty minutes, water (100 ml.) is added and the insoluble material is collected. The organic phase is washed with water (2X), 5% aqueous sodium bicarbonate (2X) and water (2X). After drying (MgSO4) the organic phase is evaporated to yield an oil. The oil is purified by chromatography on silica gel. Elution with 10% ether in benzene affords the title compound as an oil,γCHCl3Max 1720 cm-1.

Aufarbeitung

  1. additionThe reaction mixture is now diluted with 100 ml
  2. waitAfter thirty minutes
  3. customthe insoluble material is collected
  4. washThe organic phase is washed with water (2X), 5% aqueous sodium bicarbonate (2X) and water (2X)
  5. dry with materialAfter drying (MgSO4) the organic phase
  6. customis evaporated
  7. customto yield an oil
  8. customThe oil is purified by chromatography on silica gel
  9. washElution with 10% ether in benzene

Quellen und Nachweise

ORD-Eintrag
ord-a0a778b31096479bb8a13e06a5e5f06c
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04066763

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