Water → HCID 23114339, compound

HRID 2376352Notes

Reaction equation

HRID 2376352 reaction equation
[H-].[Na+].[CH:3]([C:6]1[CH:21]=[CH:20][C:9]([CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[OH:19])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].[CH3:22]I.O>CN(C=O)C>[CH:3]([C:6]1[CH:21]=[CH:20][C:9]([CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[O:19][CH3:22])=[CH:8][CH:7]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23114251HCID 23114251, compound

Product 1

HCID 23114339HCID 23114339, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixed solution of sodium hydride (a 60% liquid paraffin dispersion, 757 mg, 18.9 mmol) in DMF (50 mL) was added dropwise 2-(4-isopropylbenzyl)-3,5-dimethylphenol obtained in Reference Example 148 (4.01 g, 15.8 mmol) in DMF (15 mL) under argon atmosphere at 0° C., and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise a solution of methyl iodide (2.69 mL, 18.9 mmol) in DMF (8 mL) at the same temperature, and the mixture was stirred for 30 minutes. The reaction solution was warmed to room temperature, water was added thereto, which was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to obtain 3.49 g (yield 82%) of the title compound. Oily matter.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionwhich was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-7163ce4f6b9448d9a236dc1075b8dbef
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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