N-methoxy-N,2-dimethylbenzamide → Cyclopropyl(2-methylphenyl)methanone

HRID 1349448Notes

Reaction equation

HRID 1349448 reaction equation
CON(C)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].[CH:14]1([Mg]Br)[CH2:16][CH2:15]1.O1CCCC1.C(OCC)(=O)C.Cl>O1CCCC1>[CH3:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([CH:14]1[CH2:16][CH2:15]1)=[O:12]

Participants

5

Reactant 3

HCID 11344340N-methoxy-N,2-dimethylbenzamideHCID 21866389Hydrogen chloride-ethyl acetateHCID 178420628HCID 178420628, compound

Product 1

HCID 22382440Cyclopropyl(2-methylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-2,N-dimethylbenzamide (3.55 g) obtained in Step 1 in tetrahydrofuran (40 ml) was added dropwise a solution of 1M cyclopropylmagnesium bromide-tetrahydrofuran (29.7 ml) under ice-cooling, and the mixture was stirred at room temperature for 12 hr. To the reaction mixture was added a 4N hydrogen chloride-ethyl acetate solution (10 ml), and the resulting mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed successively with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to give the title compound (1.05 g).

Workup

  1. temperaturecooling
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed successively with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-70c93d3d9dfa4b019c7df781cabd0d43
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

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