Oxalyl chloride → 3-[1-(2-Acetoxyethyl)-3-indolyl]-4-(1-methyl-3-indolyl)furan-2,5-dione

HRID 345696Notes

Reaction equation

HRID 345696 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[C:7]([O:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)(=[O:9])[CH3:8]>ClCCl>[C:7]([O:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:8]2[C:7](=[O:9])[O:10][C:1](=[O:5])[C:2]=2[C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]([CH3:12])[CH:14]=2)=[CH:14]1)(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 151630421-(2-Acetoxyethyl)indole

Product 1

HCID 151630463-[1-(2-Acetoxyethyl)-3-indolyl]-4-(1-methyl-3-indolyl)furan-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.57 ml of oxalyl chloride were added to a solution of 5.7 g of 1-(2-acetoxyethyl)indole in 70 ml of dichloromethane at 0° C. The resulting solution was stirred for 2 hours and the solvent was then evaporated. To the residue, dissolved in 210 ml of dichloromethane, were added 7.7 ml of triethylamine and 5.29 g of 1-methylindole-3-acetic acid under a nitrogen atmosphere. After stirring for 18 hours the solvent was evaporated and the residue was purified on silica gel with ethyl acetate/petroleum ether (1:2). Crystallization from ethyl acetate/hexane gave 1.87 g of 3-[1-(2-acetoxyethyl)-3-indolyl]-4-(1-methyl-3-indolyl)furan-2,5-dione, m.p. 198°-199° C.

Workup

  1. customthe solvent was then evaporated
  2. dissolutionTo the residue, dissolved in 210 ml of dichloromethane
  3. additionwere added 7.7 ml of triethylamine and 5.29 g of 1-methylindole-3-acetic acid under a nitrogen atmosphere
  4. stirringAfter stirring for 18 hours the solvent
  5. customwas evaporated
  6. customthe residue was purified on silica gel with ethyl acetate/petroleum ether (1:2)
  7. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c3819e5d7ff648059c4570b0a64d62c9
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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