Ethyl Acetate → HCID 19808789, compound

HRID 374018Notes

Reaction equation

HRID 374018 reaction equation
[C:1]1([N:7]2[C:23](=[O:24])[C:22]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[C:18]([O:25][CH3:26])[CH:19]=5)[N:14]([CH2:27][O:28][CH3:29])[C:13]=4[C:12]([CH:30]=O)=[CH:11][C:10]=3[C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[CH3:33][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[C:1]1([N:7]2[C:23](=[O:24])[C:22]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[C:18]([O:25][CH3:26])[CH:19]=5)[N:14]([CH2:27][O:28][CH3:29])[C:13]=4[C:12]([CH:30]=[CH2:33])=[CH:11][C:10]=3[C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 638159Methyltriphenylphosphonium iodideHCID 19808856HCID 19808856, compound

Product 1

HCID 19808789HCID 19808789, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

150 mg of N-phenyl-1-formyl-6-methoxy-9-methoxymethylcarbazole-3,4-dicarboximide and 220 mg of methyltriphenylphosphonium iodide were dissolved in N,N-dimethylformamide. Thereto was added 20 mg of 60% sodium hydride with stirring under ice cooling. The resulting mixture was stirred at the same temperature for 30 minutes. To the reaction mixture were added 100 ml of ethyl acetate and 50 ml of water. The organic layer was separated, washed with 50 ml of water and an aqueous saturated sodium chloride solution in this order and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: benzene/ethyl acetate=50/1 to 20/1) to obtain 130 mg (yield: 87%) of N-phenyl-6-methoxy-9-methoxymethyl-1-vinylcarbazole-3,4-dicarboximide.

Workup

  1. stirringThe resulting mixture was stirred at the same temperature for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with 50 ml of water
  4. dry with materialan aqueous saturated sodium chloride solution in this order and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography (eluant: benzene/ethyl acetate=50/1 to 20/1)

Sources & evidence

ORD record
ord-493d2bf5f99c4fa194095961c5f5458d
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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