HCID 15390471, compound → HCID 18357814, compound

HRID 342185Notes

Reaction equation

HRID 342185 reaction equation
[CH3:1][NH2:2].CO.[O:5]=[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[C:7](OCC)=[O:8]>CO>[CH3:1][NH:2][C:7](=[O:8])[C:6](=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1

Participants

4

Reactant 2

HCID 15390471HCID 15390471, compoundHCID 57454252Monomethylamine methanol

Product 1

HCID 18357814HCID 18357814, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 40% methylamine-methanol solution (167.4 g, 2.156 mol) was added to a mixed solution of the crude ethyl α-oxo-2-(2-tetrahydropyranyloxymethyl)phenylacetate thus obtained and methanol (100 ml), and the mixture was stirred at room temperature for 40 minutes. After completion of the reaction, the mixture was concentrated under reduced pressure. Benzene (300 ml) was added to the resulting residue to filter off the insoluble materials, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain N-methyl-2-oxo-2-[2-(2-tetrahydropyranyloxymethyl)phenyl]acetamide (114.8 g, Yield: 76.8%) as an oil.

Workup

  1. customthus obtained
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionBenzene (300 ml) was added to the resulting residue
  5. filtrationto filter off the insoluble materials
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-e99a94c8cd3e47c199155a766afed572
Source dataset
uspto-grants-1999_01
Patent number
US05856573

Reaction notes

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