Dimethylformamide → HCID 53847793, compound

HRID 1417501Notes

Reaction equation

HRID 1417501 reaction equation
P(Cl)(Cl)(OCl)=O.[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:21]=2)[CH:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].CN(C)[CH:32]=[O:33]>>[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:21]=2)[C:16]([CH:32]=[O:33])=[CH:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 54217539HCID 54217539, compoundHCID 86587839Phosphoryloxychloride

Product 1

HCID 53847793HCID 53847793, compoundYield 83%

Procedure

18 mg (0.12 mmol) of phosphoryl oxychloride was added gradually to 4 ml of a solution of 25 mg (0.09 mmol) of methyl (1-benzylindol-6-yl)acetate, as obtained in a) above, in dimethyl formamide, at room temperature, and the resulting mixture was stirred for 30 minutes. After this time, an excess of a 2N aqueous solution of sodium hydroxide was added to the mixture, which was then stirred for 10 minutes. The aqueous layer was extracted with methylene chloride and the extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then the solvent was removed by evaporation under reduced pressure. The residue was subjected to column chromatography (eluent: a 25% v/v solution of ethyl acetate in hexane) to yield 23 mg (83%) of the title compound as an oil.

Workup

  1. stirringwas then stirred for 10 minutes
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. washthe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5d61b0e522584a8fa31aac706d5f07b4
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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