Water → HCID 23114302, compound

HRID 2376579Notes

Reaction equation

HRID 2376579 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[CH:15]=[C:16]([NH:19][C:20](=[O:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:17]=[CH:18][C:13]=3[O:12][C:11]2([CH3:28])[CH3:27])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[CH3:31]I.O>CN(C=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[C:14]3[CH:15]=[C:16]([N:19]([CH3:31])[C:20](=[O:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:17]=[CH:18][C:13]=3[O:12][C:11]2([CH3:28])[CH3:27])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23114223HCID 23114223, compound

Product 1

HCID 23114302HCID 23114302, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (110 mg, 290 mmol) obtained in Example 320 in DMF (3 mL) was added sodium hydride (a 60% dispersion in liquid paraffin, 12.8 mg, 319 mmol) at 0° C. and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (8.0 g, 319 mmol) was added to the reaction solution and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution and the product was extracted with diisopropyl ether. The combined extracts were washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 47 mg (yield: 41%) of the title compound. Melting point: 78-79° C. (ethyl acetate-hexane).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionthe product was extracted with diisopropyl ether
  3. washThe combined extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-fc6a9ba6d19e4c35b3e39111c7d23fe3
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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