Ethyl Acetate → [2-(Propan-2-ylsulfanyl)pyridin-3-yl]methanol

HRID 62831Notes

Reaction equation

HRID 62831 reaction equation
[CH:1]([S:4][C:5]1[N:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])([O-])(=O)=O.[Na+].[Na+].CCOC(C)=O>C1COCC1>[CH:1]([S:4][C:5]1[C:6]([CH2:7][OH:8])=[CH:10][CH:11]=[CH:12][N:13]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 152472062-(Isopropylthio)nicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 67085922[2-(Propan-2-ylsulfanyl)pyridin-3-yl]methanolYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Isopropylsulfanyl-nicotinic acid obtained in Step A was dissolved in THF (50 mL), and the solution was cooled to 0˜5° C. LAH (3.06 g, 80.55 mmol) was added thereto slowly, and the mixture was stirred at 0˜5° C. for 30 minutes and then at room temperature for 2 hours. After the termination of the reaction, saturated sodium sulfate aqueous solution was added thereto and the mixture was stirred for 30 minutes. After the addition of EtOAc, solid material was removed by using cellite. The organic layer was dried with MgSO4, filtrated and concentrated under reduced pressure. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/3) to obtain the title compound (3.94 g, 67%).

Workup

  1. temperaturethe solution was cooled to 0˜5° C
  2. waitat room temperature for 2 hours
  3. additionwas added
  4. stirringthe mixture was stirred for 30 minutes
  5. customwas removed
  6. dry with materialThe organic layer was dried with MgSO4
  7. filtrationfiltrated
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/3)

Sources & evidence

ORD record
ord-58ad80a893b540c8ab76d5f2f2dad028
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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