Diethyl Ether → HCID 13083382, compound

HRID 325875Notes

Reaction equation

HRID 325875 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:13][C:14]#N)[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=CC(C2([CH2:27][C:28]#N)CCC2)=CC=1.[Mg].C(Br)C.CC[O:36]CC>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:13][C:14](=[O:36])[CH2:27][CH3:28])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 5

HCID 3283Diethyl Ether2×HCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 13083370HCID 13083370, compoundHCID 20463011HCID 20463011, compound

Product 1

HCID 13083382HCID 13083382, compound

Procedure

A solution in ether (80 ml) of 2-[1-(3,4-dichlorophenyl)cyclobutyl]acetonitrile (23 g) prepared in a similar manner to that described in Example 1 for 2-[1-(4-chlorophenyl)cyclobutyl]acetonitrile was added to the product of the reaction between magnesium turnings (3.53 g) and ethyl bromide (10.8 ml) in dry ether (80 ml) with stirring whilst heating on a steam bath. The ether was removed and replaced with toluene and the mixture heated under reflux for one hour. Water was added and the mixture added to a mixture of ice and concentrated hydrochloric acid. The mixture was heated on a steam bath for one hour and filtered through a diatomaceous earth sold under the Registered Trade Mark CELITE. The filtrate was extracted with dichloromethane and the extract washed with water and sodium bicarbonate solution and dried. The solvent was removed by evaporation and the residue distilled to give 1-[1-(3,4-dichlorophenyl)cyclobutyl]butan-2-one (b.p. 149°-150°/1.1 mm Hg).

Workup

  1. temperaturewhilst heating on a steam bath
  2. customThe ether was removed
  3. temperaturethe mixture heated
  4. temperatureunder reflux for one hour
  5. additionWater was added
  6. additionthe mixture added to a mixture of ice and concentrated hydrochloric acid
  7. temperatureThe mixture was heated on a steam bath for one hour
  8. filtrationfiltered through a diatomaceous earth
  9. extractionThe filtrate was extracted with dichloromethane
  10. washthe extract washed with water and sodium bicarbonate solution
  11. customdried
  12. customThe solvent was removed by evaporation
  13. distillationthe residue distilled

Sources & evidence

ORD record
ord-3d4e284ab3a24036b9649794b71c3ebe
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

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