Oxalic Acid → 3-Methylindole-1-acetaldehyde

HRID 1833549Notes

Reaction equation

HRID 1833549 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][OH:13])[CH:3]=1.FC(F)(F)C(O)=O.N1C=CC=CC=1.C(O)(=O)C(O)=O>CS(C)=O.C1C=CC=CC=1.CCOCC.CO.O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH:12]=[O:13])[CH:3]=1

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 122267423-Methylindole-1-ethanol

Product 1

HCID 545647933-Methylindole-1-acetaldehyde

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 18518713Benzene dimethylsulfoxideSolvent

Procedure

N,N-dicyclohexylcarbodiimide (9.0 g) is added to a cooled, stirred solution of 3-methylindole-1-ethanol (3.0 g) in 30 ml of dimethyl sulfoxide-benzene(2:1) containing trifluoroacetic acid (0.6 ml) and pyridine (1.12 ml). The reaction is stirred at room temperature under nitrogen for 5 hours. The reaction mixture is now diluted with 300 ml of ether, followed by the dropwise addition of a solution of oxalic acid (3.78 g) in 11 ml of methanol. After thirty minutes, water (300 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 3-methylindole-1-acetaldehyde. The latter compound is then converted to its corresponding gem-dithiol with hydrogen sulfide and reduced with lithium aluminium hydride according to the method of T. L. Cairns et al., J. Amer. Chem. Soc., 74, 3982 (1952), to yield the title compound, γmaxCHCl3 2570 cm-1.

Workup

  1. waitAfter thirty minutes
  2. customthe insoluble material is collected
  3. washThe organic phase is washed with water (2X), 5% aqueous sodium bicarbonate (2X) and water (2X)
  4. dry with materialAfter drying (MgSO4) the organic phase
  5. customis evaporated

Sources & evidence

ORD record
ord-88a44e35b572455fb4fbf00f9317c515
Source dataset
uspto-grants-1978_01
Patent number
US04066763

Reaction notes

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