Diethyl Ether → HCID 19031557, compound

HRID 266869Notes

Reaction equation

HRID 266869 reaction equation
C[Mg]I.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2(C#N)[CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1.CC[O:19][CH2:20][CH3:21]>>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2([C:20](=[O:19])[CH3:21])[CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 219019791-(3-Chlorophenyl)cyclobutane-1-carbonitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 19031557HCID 19031557, compound

Procedure

Methylmagnesium iodide (138 ml of 3M solution in ether) was added dropwise to a stirred solution of 1-(3-chlorophenyl)cyclobutanecarbonitrile (53 g) in ether (100 ml) under nitrogen at 0° C. The mixture was stirred at ambient temperature for 24 hours. The resulting solid was collected by filtration, washed well with ether, then added in portions to an ice-cold mixture of water (200 ml) and concentrated hydrochloric acid (125 ml). The resulting yellow suspension was heated at 95° C. for 1 hour with occasional stirring, and then cooled to ambient temperature. The product was extracted into ether (5×100 ml) and the combined extracts washed with water (2×100 ml), dried over magnesium sulphate and the solvent removed in vacuo to give an oil which was distilled to give 1-[1-(3-chlorophenyl)cyclobutyl]ethanone (47.5 g), b.p. 108°-109° C./2 mbar.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed well with ether
  3. additionadded in portions to an ice-cold mixture of water (200 ml) and concentrated hydrochloric acid (125 ml)
  4. temperatureThe resulting yellow suspension was heated at 95° C. for 1 hour with occasional stirring
  5. temperaturecooled to ambient temperature
  6. extractionThe product was extracted into ether (5×100 ml)
  7. washthe combined extracts washed with water (2×100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customthe solvent removed in vacuo
  10. customto give an oil which
  11. distillationwas distilled

Sources & evidence

ORD record
ord-8a2604b401f94b869a3d925cd50eb68c
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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