Water → HCID 70242352, compound

HRID 617390Notes

Reaction equation

HRID 617390 reaction equation
ClC[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([O:14][CH3:15])[C:10]([NH:12][CH3:13])=[O:11].[CH3:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[OH:25].[H-].[Na+].O.[CH3:29]N(C)C=O>>[CH3:15][O:14][C:9]([CH2:29][O:25][C:18]1[CH:19]=[C:20]([CH3:24])[CH:21]=[C:22]([CH3:23])[C:17]=1[CH3:16])([C:4]1[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([NH:12][CH3:13])=[O:11]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 127692,3,5-TrimethylphenolHCID 24758Sodium hydrideHCID 70243626HCID 70243626, compound

Product 1

HCID 70242352HCID 70242352, compoundYield 50%

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloromethyl-α-methoxy-N-methyl-phenylacetamide (0.25 g, 1.1 mmol) and 2,3,5-trimethylphenol (0.18 g, 1.3 mmol) in N,N-dimethylformamide (3 ml) was stirred at 0° C., and 60% oily sodium hydride (0.08 g, 2.0 mmol) was added thereto. The mixture was stirred at 0° C. for 70 minutes and then at room temperature for 1 hour, and ice and water were added in this order. The mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7/3) to give the desired compound α-methoxy-N-methyl-(2,3,5-trimethylphenoxymethyl)phenylacetamide (0.17 g, 50%) as an oil.

Workup

  1. waitat room temperature for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-a295ed93e4774e888520f45923ee79c9
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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