HCID 23128496, compound → HCID 63351291, compound

HRID 1468259Notes

Reaction equation

HRID 1468259 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9](N(OC)C)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:15]1([Mg]Br)[CH2:17][CH2:16]1>C1COCC1>[CH:1]1([CH2:7][CH2:8][C:9]([CH:15]2[CH2:17][CH2:16]2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 23128496HCID 23128496, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 63351291HCID 63351291, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Cyclohexyl-N-methoxy-N-methylpropaneamide (100 mg, 0.502 mmol) obtained in step 1 was dissolved in THF (1.0 mL). Under ice-cooled condition, cyclopropylmagnesium bromide (0.5 mol/L THF solution) (1.20 mL, 0.600 mmol) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was extracted with ethyl acetate after adding a saturated ammonium chloride aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20) to give 3-cyclohexyl-1-cyclopropylpropan-1-one (61.7 mg, yield 68%).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. additionafter adding a saturated ammonium chloride aqueous solution
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20)

Sources & evidence

ORD record
ord-3c7d608d439345bfbbeb161d6e488d9b
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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