Dimethylformamide → HCID 23020364, compound

HRID 917368Notes

Reaction equation

HRID 917368 reaction equation
CN(C)C=O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:26])=[C:23]([F:25])[F:24])=[O:16].[CH2:27](I)[CH3:28].[H-].[Na+]>O>[CH2:27]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:26])=[C:23]([F:24])[F:25])=[O:16])[CH3:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 23020240HCID 23020240, compound

Product 1

HCID 23020364HCID 23020364, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 ml of N,N-dimethylformamide were dissolved 0.32 g (1.1 mmol) of 6,6-difluoro-5-methyl-5-hexenyl 1H-indole-2-carboxylate and 0.34 g (2.2 mmol) of ethyl iodide, followed by the addition of 0.06 g (1.5 mmol) of sodium hydride at room temperature and stirring at the same temperature for 1 hour. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:5) to obtain 0.31 g (yield: 88%) of 6,6-difluoro-5-methyl-5-hexenyl 1-ethyl-1H-indole-2-carboxylate.

Workup

  1. customThe reaction liquid
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-d8eede826a7643c3b3099b3a3a25c898
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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