4,4-Difluoro-N-methoxy-N-methylcyclohexanecarboxamide → 1-(4,4-Difluorocyclohexyl)ethan-1-one

HRID 406031Notes

Reaction equation

HRID 406031 reaction equation
[CH3:1][Li].CON(C)[C:6]([CH:8]1[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10][CH2:9]1)=[O:7]>C1COCC1>[F:14][C:11]1([F:15])[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[CH3:1])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 584217634,4-Difluoro-N-methoxy-N-methylcyclohexanecarboxamideHCID 178418348HCID 178418348, compound

Product 1

HCID 143656631-(4,4-Difluorocyclohexyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 ml methyl lithium (1 M in diethylether) were added into a solution of 0.593 g 4,4-difluoro-cyclohexanecarboxylic acid methoxy-methyl-amide in anhydrous 5 ml THF at 0° C. The reaction was allowed to warm to rt overnight. The reaction was quenched with sat. ammonium chloride solution (˜50 ml) and diluted with sat. sodium hydrogencarbonate solution (25 ml). The aqueous layer was extracted with diethylether (3×50 ml) and the combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. Purification was achieved by silica gel column chromatography (solvent: 5:1→1:1 petroleum/ether (40-60).

Workup

  1. customThe reaction was quenched with sat. ammonium chloride solution (˜50 ml)
  2. additiondiluted with sat. sodium hydrogencarbonate solution (25 ml)
  3. extractionThe aqueous layer was extracted with diethylether (3×50 ml)
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-4c57a43b19f749ab907a69f495ea70ab
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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