Water → (2-Butylsulfanyl-pyridin-3-yl)-methanol

HRID 62850Notes

Reaction equation

HRID 62850 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([S:11][C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](O)=[O:15])[CH2:8][CH2:9][CH3:10].O>C1COCC1>[CH2:7]([S:11][C:12]1[C:13]([CH2:14][OH:15])=[CH:17][CH:18]=[CH:19][N:20]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 167837802-Butylsulfanyl-nicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 90118243(2-Butylsulfanyl-pyridin-3-yl)-methanolYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous THF (30 mL) in dried flask was cooled to 0° C., LAH (1.14 g, 30 mmol) was added slowly thereto, and the mixture was stirred for 30 minutes. 2-Butylsulfanyl-nicotinic acid (1.27 g, 5.58 mmol) obtained in Step A which is dissolved in anhydrous THF (10 mL) was added slowly thereto, and the mixture was stirred at room temperature for 2 hours. After the termination of the reaction, water (10 mL) was added slowly thereto at 0° C., and the mixture was stirred for 30 minutes. The reactant was extracted with EtOAc, and the organic layer was separated, dried with MgSO4, and concentrated under reduced pressure to obtain the title compound (0.85 g, 77%).

Workup

  1. additionwas added slowly
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. additionwas added slowly
  4. stirringat 0° C., and the mixture was stirred for 30 minutes
  5. extractionThe reactant was extracted with EtOAc
  6. customthe organic layer was separated
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc9e0989051e413cb5dc5189dc8ba50f
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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