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

HRID 596959

反応式

HRID 596959 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a89ae027ab344a3392a21ec502830c06
出典データセット
uspto-grants-1977_03
特許番号
US04012511

関連ノート

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