Water → (6-Sec-butylsulfanyl-pyridin-2-yl)-methanol

HRID 62840Notes

Reaction equation

HRID 62840 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12][CH:13]([CH2:15][CH3:16])[CH3:14])[N:7]=1)=O)C.[Li+].[BH4-].O>C1COCC1>[CH:13]([S:12][C:8]1[N:7]=[C:6]([CH2:4][OH:3])[CH:11]=[CH:10][CH:9]=1)([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 901182566-Sec-butylsulfanyl-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 90118289(6-Sec-butylsulfanyl-pyridin-2-yl)-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

6-sec-Butylsulfanyl-pyridine-2-carboxylic acid ethyl ester (0.17 g, 0.71 mmol) obtained in Step A was dissolved in anhydrous THF (3 mL). 2.0 M LiBH4 solution (0.5 mL, 1.0 mmol) was added thereto, and the mixture was stirred at 40° C. for 1 hour. After the termination of the reaction, the reactant was cooled to room temperature. The reactant was added with water and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, and concentrated under reduced pressure to obtain the title compound (0.126 g, 90%).

Workup

  1. customAfter the termination of the reaction
  2. temperaturethe reactant was cooled to room temperature
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c405c0f80fc440a97b9ac682ac47e2a
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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