Dimethylformamide → HCID 69179501, compound

HRID 917367Notes

Reaction equation

HRID 917367 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.N1C2[C:9](=[CH:10][C:11]([C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:26])=[C:23]([F:25])[F:24])=[O:16])=[CH:12][CH:13]=2)[CH:8]=C1.CI.[H-].[Na+]>O>[CH3:1][N:2]1[C:5]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:26])=[C:23]([F:24])[F:25])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69181661HCID 69181661, compound

Product 1

HCID 69179501HCID 69179501, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 ml of N,N-dimethylformamide were dissolved 0.40 g (1.4 mmol) of 6,6-difluoro-5-methyl-5-hexenyl 1H-indole-5-carboxylate and 0.40 g (2.8 mmol) of methyl iodide, followed by the addition of 0.07 g (1.7 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 0.36 g (yield: 86%) of 6,6-difluoro-5-methyl-5-hexenyl 1-methyl-1H-indole-5-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-be5c4a55c15f4c8698696bbdea0276db
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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