Ammonia → (4-(2-(Pyridin-4-YL)vinyl)phenyl)methanol

HRID 2287590Notes

Reaction equation

HRID 2287590 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.N.CO>O1CCCC1>[N:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:23][CH:24]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 12006312methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 70240750(4-(2-(Pyridin-4-YL)vinyl)phenyl)methanolYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (92.8 mg) in tetrahydrofuran (12 ml) was added methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoate (1.17 g), and after stirring for 2 hours at ambient temperature, ammonia solution and methanol were added thereto. The mixture was stirred for 2 hours at ambient temperature. Insoluble material was filtered off, and the filtrate was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized with diisopropyl ether to give 4-[(E)-2-(4-pyridyl)vinyl]benzyl alcohol (762 mg).

Workup

  1. stirringThe mixture was stirred for 2 hours at ambient temperature
  2. filtrationInsoluble material was filtered off
  3. washthe filtrate was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized with diisopropyl ether

Sources & evidence

ORD record
ord-5b5bdac272474d4bafedcbbccb1c56b4
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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