Diethyl Ether → HCID 21258427, compound

HRID 635353Notes

Reaction equation

HRID 635353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:14]([Mg]Br)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Br)CC1C=CC=CC=1.[Mg].CC[O:36]CC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=[O:36])[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 7666Phenethyl bromideHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 5462224MagnesiumHCID 178419670HCID 178419670, compound

Product 1

HCID 21258427HCID 21258427, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(4-chlorophenyl)cyclobutanecarbonitrile (35 g) in toluene (100 ml) was added dropwise at reflux temperature under nitrogen to a stirred solution of phenethylmagnesium bromide [prepared in the usual manner from phenethyl bromide (45.6 g) and magnesium (6.24 g)] in ether (100 ml). When the addition was completed, ether was distilled from the mixture until the internal temperature rose to 110° C., then stirring at this temperature was continued for 18 hours. The mixture was then cooled to ambient temperature, added to a mixture of ice (200 g) and concentrated hydrochloric acid (100 ml), heated at 95° C. with occasional stirring for 4 hours, and cooled to ambient temperature. The product was extracted into dichloromethane (3×200 ml), and the combined extracts were washed with water (100 ml), saturated aqueous sodium carbonate solution (2×100 ml) and water (100 ml), dried (Na2SO4), and the solvent was removed in vacuo. The residue was distilled to give 1-[1-(4-chlorophenyl)cyclobutyl]-3-phenylpropan-1-one as a yellow oil (38.8 g), b.p. 178-181° C./1.3 mbar.

Workup

  1. additionWhen the addition
  2. distillationether was distilled from the mixture until the internal temperature
  3. customrose to 110° C.
  4. additionadded to a mixture of ice (200 g) and concentrated hydrochloric acid (100 ml)
  5. temperatureheated at 95° C.
  6. stirringwith occasional stirring for 4 hours
  7. temperaturecooled to ambient temperature
  8. extractionThe product was extracted into dichloromethane (3×200 ml)
  9. washthe combined extracts were washed with water (100 ml), saturated aqueous sodium carbonate solution (2×100 ml) and water (100 ml)
  10. dry with materialdried (Na2SO4)
  11. customthe solvent was removed in vacuo
  12. distillationThe residue was distilled

Sources & evidence

ORD record
ord-60a517525dab4c189ecf01f0e6f76979
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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