Dimethylformamide → HCID 19779200, compound

HRID 2081957Notes

Reaction equation

HRID 2081957 reaction equation
[H-].[Na+].[CH3:3][C:4]([C:7]1[C:15]2[O:14][C:13](=O)[CH2:12][C:11]=2[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=1)([CH3:6])[CH3:5].I[CH3:20].CN(C)[CH:23]=[O:24]>O>[CH3:13][C:12]1([CH3:20])[C:11]2[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=[C:7]([C:4]([CH3:6])([CH3:5])[CH3:3])[C:15]=2[O:14][C:23]1=[O:24]

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22507799HCID 22507799, compound

Product 1

HCID 19779200HCID 19779200, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 400 ml of N,N-dimethylformamide (DMF) was suspended 60.7 g of 60% sodium hydride followed by dropwise addition of a solution of 7-(1,1-dimethylethyl)-5-methoxy-2(3H)-benzofuranone (160 g) in DMF (1000 ml) at a temperature not exceeding 50° C. and the mixture was stirred for 30 minutes. Then, a solution of iodomethane (230 g) in DMF (100 ml) was added and the mixture was stirred at ambient temperature for 3 hours. The reaction mixture was poured in water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The resultant crude product was purified by silica gel column chromatography ( ethyl acetate-hexane =1:10) and washed with cold hexane to give 104 g of 3,3-dimethyl-7-(1,1-dimethylethyl)-5-methoxy-2(3H)-benzofuranone as a light yellow solid.

Workup

  1. customexceeding 50° C.
  2. stirringthe mixture was stirred at ambient temperature for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resultant crude product was purified by silica gel column chromatography ( ethyl acetate-hexane =1:10)
  8. washwashed with cold hexane

Sources & evidence

ORD record
ord-09bf36ba987e4d84bb2720e9abda0630
Source dataset
uspto-grants-1993_02
Patent number
US05187161

Reaction notes

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