Diethyl Ether → HCID 15728457, compound

HRID 1463371Notes

Reaction equation

HRID 1463371 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.[Mg].[CH3:11][N:12]([CH3:23])[C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[O:16][CH2:17][C:18]#N.CC[O:26]CC>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:18](=[O:26])[CH2:17][O:16][C:15]2[CH:20]=[CH:21][CH:22]=[C:13]([N:12]([CH3:23])[CH3:11])[CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether3×HCID 12103m,alpha-DichlorotolueneHCID 5462224MagnesiumHCID 150774072-[3-(Dimethylamino)phenoxy]acetonitrile

Product 1

HCID 15728457HCID 15728457, compound

Conditions

Temperature
0 °C

Procedure

A solution of 10.0 g of 3-chlorobenzyl chloride in 75 ml of dry ether was added slowly to 2.25 g of magnesium powder in 75 ml of dry ether under nitrogen. The Grignard reagent was stirred at ambient temperature for one hour and then added to a solution of 5.47 g of 3-(dimethylamino)phenoxyacetonitrile in 200 ml of dry ether stirred at 0° C. The reaction was warmed to room temperature overnight and then quenched with of NH4Cl solution. The mixture was diluted with of water and the layers separated. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography (silica gel; 8:1 hexane-ethyl acetate) and recrystallized from ethyl acetate-hexane to give 4.3 g of 1-(3-chlorophenyl)-3-[3-dimethylamino)phenoxy]-2-propanone, m.p. 82°-83° C.

Workup

  1. temperatureThe reaction was warmed to room temperature overnight
  2. customquenched with of NH4Cl solution
  3. additionThe mixture was diluted with of water
  4. customthe layers separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (silica gel; 8:1 hexane-ethyl acetate)
  10. customrecrystallized from ethyl acetate-hexane
  11. customto give 4.3 g of 1-(3-chlorophenyl)-3-[3-dimethylamino)phenoxy]-2-propanone, m.p. 82°-83° C.

Sources & evidence

ORD record
ord-0c2249ed96374f6d99d3a05f55ac9ce8
Source dataset
uspto-grants-1994_04
Patent number
US05300527

Reaction notes

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