Water → (6-Isopropylsulfanyl-pyridin-2-yl)-methanol

HRID 62859Notes

Reaction equation

HRID 62859 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][CH:12]([CH3:14])[CH3:13])[N:6]=1)=O.[Li+].[BH4-].O>C1COCC1>[CH:12]([S:11][C:7]1[N:6]=[C:5]([CH2:3][OH:2])[CH:10]=[CH:9][CH:8]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 901182976-Isopropylsulfanyl-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 90118332(6-Isopropylsulfanyl-pyridin-2-yl)-methanolYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

6-Isopropylsulfanyl-pyridine-2-carboxylic acid methyl ester (0.13 g, 0.61 mmol) obtained in Step A was dissolved in anhydrous THF (3 mL). 2.0M LiBH4 solution (0.5 mL, 1 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, added with water, and extracted with EtOAc. The organic layer was separated, dried with MgSO4, and concentrated under reduced pressure to obtain the title compound (0.08 g, 70%).

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-23a03f644c474fe882bd4eaf80e0accb
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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