Sodium sulfate decahydrate → (5-Phenylpyridin-3-yl)methanol

HRID 349967Notes

Reaction equation

HRID 349967 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[CH:14]=[C:15]([C:19](OCC)=[O:20])[CH:16]=[N:17][CH:18]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:7]1([C:13]2[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[N:17][CH:18]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 15530815Ethyl 5-phenylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 22254272(5-Phenylpyridin-3-yl)methanolYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1.45 g) was added to a solution of ethyl 5-phenyl-3-pyridinecarboxylate (8.60 g) in tetrahydrofuran (100 ml) at 0° C., which was stirred at room temperature for 30 minutes. Sodium sulfate decahydrate (13.40 g) was added to the reaction mixture, which was stirred at room temperature for 30 minutes. The precipitate was removed by filtration, and the filtrate was concentrated. The resulting colorless crystals were collected by filtration to obtain 5-phenyl-3-pyridylmethanol (4.82 g, yield 69%). This was recrystallized from ethyl acetate-hexane. Melting point: 71–72° C.

Workup

  1. stirringwas stirred at room temperature for 30 minutes
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-9c9b549899e848bba36a68dc211598ff
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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