Dimethylformamide → HCID 86753760, compound

HRID 1417423Notes

Reaction equation

HRID 1417423 reaction equation
[H-].[Na+].CN(C)C=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:19])=[C:13]2[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[CH3:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>CCCCCC.C(OCC)(=O)C.O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:34](=[O:35])[C:33]1[CH:37]=[CH:38][C:30]([O:29][CH3:28])=[CH:31][CH:32]=1)[C:14]([CH3:19])=[C:13]2[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7477p-Anisoyl chlorideHCID 24758Sodium hydrideHCID 600108HCID 600108, compound

Product 1

HCID 86753760HCID 86753760, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

Combine sodium hydride (0.66 g, 60% in oil, 13.1 mmol) and dimethylformamide [50 mL). Cool to 0° C. using an ice-bath. Add t-butyl (5-methoxy-2-methyl-indol-3-yl]-acetate (3 g, 10.9 mmol). Stir until gas evolution ceases. Add 4-methoxybenzoyl chloride (2.23 g, 13 mmol). Warm to ambient temperature. After 18 hours, add water. Partition the reaction mixture between ethyl acetate and water. Separate the organic layer and extract with a saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/4 ethyl acetate hexane to give the title compound.

Workup

  1. temperatureWarm to ambient temperature
  2. customPartition the reaction mixture between ethyl acetate and water
  3. customSeparate the organic layer
  4. extractionextract with a saturated sodium chloride solution
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-0919d2c3cb2f4e9ab1641963e07abae9
Source dataset
uspto-grants-1999_03
Patent number
US05877202

Reaction notes

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