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

HRID 596959

반응식

HRID 596959 반응식
[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.CS(C)=O.C1C=CC=CC=1.FC(F)(F)C(O)=O.C(O)(=O)C(O)=O>O.CO.CCOCC.N1C=CC=CC=1>[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

참가 물질

9

반응물 4

HCID 971Oxalic AcidHCID 6422Trifluoroacetic acidHCID 18518713Benzene dimethylsulfoxideHCID 213895531,10-Dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole-1-propanol

생성물 1

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

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 1049Pyridine용매HCID 3283Diethyl Ether용매

실험 절차

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 sulfoxide-benzene (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.

후처리

  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

출처 및 근거

ORD 기록
ord-a89ae027ab344a3392a21ec502830c06
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04012511

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