Diethyl Ether → HCID 68133257, compound

HRID 1606496Notes

Reaction equation

HRID 1606496 reaction equation
C([N-]C(C)C)(C)C.[Li+].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1.[C:16](OC)(=[O:25])[C:17]1[CH:22]=[CH:21][C:20](OC)=[CH:19][CH:18]=1.[Li].C[CH2:30][O:31]CC>O>[CH3:30][O:31][C:12]1[CH:13]=[CH:14][N:9]=[CH:10][C:11]=1[CH2:15][C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:25]

Participants

7

Reactant 5

HCID 3283Diethyl Ether2×HCID 79703-MethylpyridineHCID 8499Methyl anisateHCID 2724682Lithium diisopropylamideHCID 3028194Lithium

Product 1

HCID 68133257HCID 68133257, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3 moles of lithium diisopropylamide in 3 liters ether is added 3 moles of β-picoline. After 1/2 hour, a solution of 1 mole methyl anisate in ether is added dropwise. After 1 hour under reflux, the mixture is cooled and decomposed with water. After all the lithium has dissolved, the layers are separated. The organics are washed with water, dried (magnesium sulfate) and distilled. The product is collected at 155°-165°C at 0.3 mm Hg and recrystallized from benzene-pet ether to yield 88 g (39%) 4-methoxy-α-(3-pyridyl)-acetophenone. [Miller, Osuch, Goldberg, and Levine, JACS, 78, 674 (1956) and Raynolds and Levine, JACS, 82, 472 (1960)].

Workup

  1. temperatureAfter 1 hour under reflux
  2. temperaturethe mixture is cooled
  3. customthe layers are separated
  4. washThe organics are washed with water
  5. dry with materialdried (magnesium sulfate)
  6. distillationdistilled
  7. customThe product is collected at 155°-165°C at 0.3 mm Hg
  8. customrecrystallized from benzene-pet ether

Sources & evidence

ORD record
ord-980bf72d293a4953a474c7edaab6fbe4
Source dataset
uspto-grants-1976_04
Patent number
US03953434

Reaction notes

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