Methanol → HCID 18780288, compound

HRID 345675Notes

Reaction equation

HRID 345675 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18](=[O:32])O[C:20](=[O:31])[C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[CH:9]1)(=[O:3])[CH3:2].C[Si](C)(C)[NH:35][Si](C)(C)C.CO>C(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18](=[O:32])[NH:35][C:20](=[O:31])[C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[CH:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887Methanol3×HCID 13838Hexamethyldisilazane3×HCID 18780267HCID 18780267, compound

Product 1

HCID 18780288HCID 18780288, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 0.411 g of 3-[1-(3-acetoxypropyl)-3-indolyl]-4-(2-nitrophenyl)furan-2,5-dione in 50 ml of chloroform was treated with a mixture of 1.53 g of 1,1,1,3,3,3-hexamethyldisilazane and 0.3 g of methanol and the mixture was heated at 60° C. for 1 hour. A further 1.53 g of hexamethyldisilazane and a further 0.3 g of methanol were added and the heating was continued overnight before adding further 1.53 g of hexamethyldisilazane and 0.3 g of methanol. The mixture was heated for a further 1 hour. The solvents were removed under reduced pressure and the residue was chromatographed on silica gel with 5% methanol in dichloromethane to give 130 mg of 3-[1-(3-acetoxypropyl)-3-indolyl]-4-(2-nitrophenyl)-1H-pyrrole-2,5-dione, m.p. 77°-78° C.

Workup

  1. temperatureThe mixture was heated for a further 1 hour
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was chromatographed on silica gel with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-9965c574484749a0a7bcff568780a9a5
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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