Sodium sulfate decahydrate → (4-Chloro-2,6-dimethylpyridin-3-yl)methanol

HRID 591510Notes

Reaction equation

HRID 591510 reaction equation
[Cl:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([CH3:14])[CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:14])[N:5]=[C:6]([CH3:13])[C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 239536Ethyl 4-chloro-2,6-dimethylnicotinateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 89767886(4-Chloro-2,6-dimethylpyridin-3-yl)methanolYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of ethyl 4-chloro-2,6-dimethylnicotinate (1.5 g) and THF (50 mL) was added diisobutylaluminum hydride (1M in toluene, 42.0 mL) at 0° C. After stirring at room temperature for 1 h, sodium sulfate decahydrate (13.5 g) and THF were added to the mixture and the mixture was stirred at room temperature for 3 h. The mixture was passed through Celite®. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (0.920 g). The obtained crystals were recrystallized from EtOAc-hexane.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 h
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-0ba81a657612478b96d8a848ab8091f8
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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