Tetrahydrofuran → HCID 19092856, compound

HRID 487663Notes

Reaction equation

HRID 487663 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][C:13]([C:20]([OH:22])=[O:21])=[C:12]2[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1.O1[CH2:37][CH2:36][CH2:35]C1>CN(C)C=O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][C:13]([C:20]([O:22][C:36]([CH3:35])([CH3:37])[CH3:1])=[O:21])=[C:12]2[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 19092862HCID 19092862, compound

Product 1

HCID 19092856HCID 19092856, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

N,N-Dimethylformamide (3 drops) and oxalyl chloride (0.59 ml) were added to a solution of 5,6-dimethoxy-3-(3,4-dimethoxyphenyl)indole-2-carboxylic acid (2.0 g) in tetrahydrofuran (50 ml). The mixture was stirred for an hour at room temperature and concentrated under reduced pressure. The residue was dissolved in benzene (20 ml). This benzene solution was added to a solution of tert-butanol (0.79 ml) and N,N-dimethylaniline (0.85 ml) in benzene (30 ml), followed by stirring overnight at room temperature. The mixture was successively washed with water, sodium hydrogen carbonate saturated aqueous solution and water, dried (MgSO4) and concentrated. The precipitated crystals were collected by filtration and recrystallized from acetone to give tert-butyl 5,6-dimethoxy-3-(3,4-dimethoxyphenyl)indole-2-carboxylate (1.61 g, 70%) as colorless prisms.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in benzene (20 ml)
  3. additionThis benzene solution was added to a solution of tert-butanol (0.79 ml) and N,N-dimethylaniline (0.85 ml) in benzene (30 ml)
  4. stirringby stirring overnight at room temperature
  5. washThe mixture was successively washed with water, sodium hydrogen carbonate saturated aqueous solution and water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. filtrationThe precipitated crystals were collected by filtration
  9. customrecrystallized from acetone

Sources & evidence

ORD record
ord-d6691a02d6bb4bde938660d0c6ea2810
Source dataset
uspto-grants-1994_03
Patent number
US05296499

Reaction notes

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