Diethyl Ether → HCID 13243717, compound

HRID 614119Notes

Reaction equation

HRID 614119 reaction equation
[C:1]1([CH2:7][CH2:8]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].[CH3:11][C:12]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[CH:17]=1)([CH3:15])[C:13]#N.CC[O:28]CC>>[CH3:15][C:12]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[CH:17]=1)([C:13](=[O:28])[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:11]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 7666Phenethyl bromideHCID 5462224MagnesiumHCID 97942622-(3,5-dimethoxyphenyl)-2-methylpropanenitrile

Product 1

HCID 13243717HCID 13243717, compound

Procedure

To a solution of the Grignard reagent prepared from 2-phenylbromoethane (5.5 g.), magnesium (0.8 g.) and dry ether (60 ml.) is added a solution of 2-methyl-2-(3,5-dimethoxyphenyl)propionitrile (2.75 g.) in dry ether (20 ml.). The ether is distilled off and replaced by dry benzene (50 ml.) and the mixture refluxed for 48 hours. It is then decomposed by careful treatment with dilute sulfuric acid and heated on a steam bath for 1 hour. The mixture is then extracted with ether, the extract dried (MgSO4) and concentrated to an oil. Distillation of the oil in vacuo affords 2-methyl-2-(3,5-dimethoxyphenyl)-5-phenyl-3-pentanone; b.p. 168° C./0.2 mm. (Yield: 2.32 g., 60%)

Workup

  1. distillationThe ether is distilled off
  2. temperaturethe mixture refluxed for 48 hours
  3. temperatureheated on a steam bath for 1 hour
  4. extractionThe mixture is then extracted with ether
  5. dry with materialthe extract dried (MgSO4)
  6. concentrationconcentrated to an oil
  7. distillationDistillation of the oil in vacuo

Sources & evidence

ORD record
ord-342bd9d1a30e4660b58e6fb05d87e412
Source dataset
uspto-grants-1979_03
Patent number
US04143139

Reaction notes

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