Diethyl Ether → 2-(2-CHLOROPHENYL)-1-CYCLOPROPYLETHAN-1-ONE

HRID 1975698Notes

Reaction equation

HRID 1975698 reaction equation
[Mg].[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Br.[CH:11]1([C:14]#N)[CH2:13][CH2:12]1.[Cl-].[NH4+].C([O:20]CC)C>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:11]1([C:14]([CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[Cl:2])=[O:20])[CH2:13][CH2:12]1

Participants

8

Reactant 5

HCID 3283Diethyl Ether3×HCID 11905alpha-Bromo-o-chlorotolueneHCID 25517Ammonium ChlorideHCID 79637CyclopropanecarbonitrileHCID 5462224Magnesium

Product 1

HCID 199195022-(2-CHLOROPHENYL)-1-CYCLOPROPYLETHAN-1-ONE

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

10 ml of anhydrous diethyl ether were added to 0.45 g (18.5 mmole) of metallic magnesium, and then a solution of 2.0 ml (15.4 mmole) of 2-chlorobenzyl bromide in 10 ml of diethyl ether was slowly added dropwise to the resulting mixture, whilst stirring; the mixture was then stirred at room temperature for one hour. The resulting solution was slowly added dropwise to a solution of 1.1 ml of cyclopropyl cyanide in 10 ml of diethyl ether over a period of 30 minutes, and then the mixture was stirred at room temperature for 2 hours. At the end of this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the mixture was stirred at room temperature for 15 minutes. 200 ml of ethyl acetate were then added to the reaction mixture, and the organic layer was separated, washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, and dried over anhydrous sodium sulfate; the solvent was then removed by distillation under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, using a 9:1 by volume mixture of toluene and ethyl acetate as the eluent, to give 2.0 g of the title compound as a colorless oil.

Workup

  1. stirringthe mixture was then stirred at room temperature for one hour
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. stirringthe mixture was stirred at room temperature for 15 minutes
  4. customthe organic layer was separated
  5. washwashed with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was then removed by distillation under reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-852884749b5741709d60958ca1163af9
Source dataset
uspto-grants-1994_02
Patent number
US05288726

Reaction notes

Loading…