Sodium sulfate decahydrate → HCID 17930185, compound

HRID 349964Notes

Reaction equation

HRID 349964 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[N:17]2[CH:18]=[C:19]([CH2:21][O:22][C:23]3[CH:28]=[C:27]([C:29](OC)=[O:30])[CH:26]=[CH:25][N:24]=3)[N:20]=[C:16]2[CH:15]=[CH:14][CH:13]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:11][C:12]1[N:17]2[CH:18]=[C:19]([CH2:21][O:22][C:23]3[CH:28]=[C:27]([CH2:29][OH:30])[CH:26]=[CH:25][N:24]=3)[N:20]=[C:16]2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 23024901HCID 23024901, compound

Product 1

HCID 17930185HCID 17930185, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminium hydride (1.0M tetrahydrofuran solution, 30 ml) was added to a solution of methyl 2-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)-4-pyridinecarboxylate (3.97 g) in tetrahydrofuran (150 ml) at 0° C., which was stirred at room temperature for 30 minutes. Sodium sulfate decahydrate (12.2 g) was added to the reaction mixture, which was stirred at room temperature for 1 hour. The precipitate was removed by filtration, and the filtrate was concentrated. The resulting colorless crystals were collected by filtration to obtain 2-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)-4-pyridylmethanol (3.12 g, yield 86%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 143–144° C.

Workup

  1. stirringwas stirred at room temperature for 1 hour
  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-a1455cf2133a40e5a042da0be516a0bb
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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