Isopropyl iodide → [2-(Propan-2-ylsulfanyl)pyridin-3-yl]methanol

HRID 384114Notes

Reaction equation

HRID 384114 reaction equation
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[H-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].I[CH:37]([CH3:39])[CH3:38]>CN(C)C=O.[Cl-].[NH4+].O1CCCC1>[CH:37]([S:1][C:2]1[C:3]([CH2:4][OH:6])=[CH:7][CH:8]=[CH:9][N:10]=1)([CH3:39])[CH3:38]

Participants

9

Reactant 5

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 178524460HCID 178524460, compound

Product 1

HCID 67085922[2-(Propan-2-ylsulfanyl)pyridin-3-yl]methanol

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-mercaptonicotinic acid (700 mg) in dimethylformamide (7 ml), 1.35 ml of 2-iodopropane and 541 mg of sodium hydride were added under ice-cooling, and the reaction solution was stirred at room temperature for 4 hours, at 60° C. for 2 hours. The reaction solution was cooled, then diluted with a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of lithium aluminum hydride (428 mg) in tetrahydrofuran (7 ml), a solution of the crude product in tetrahydrofuran (3 ml) was added under ice-cooling, and the reaction solution was stirred at the same temperature for 30 minutes. To the reaction solution was added sodium sulfate decahydrate, and the mixture was further stirred at the same temperature for 1 hour. The reaction solution was Celite-filtered, the filtrate was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50:50)) to afford the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. temperatureThe reaction solution was cooled
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto afford a crude product as a yellow oil
  8. temperaturecooling
  9. stirringthe reaction solution was stirred at the same temperature for 30 minutes
  10. stirringthe mixture was further stirred at the same temperature for 1 hour
  11. filtrationThe reaction solution was Celite-filtered
  12. distillationthe filtrate was distilled off under reduced pressure
  13. customthe residue obtained
  14. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50:50))

Sources & evidence

ORD record
ord-cdbb1d5e62074f438465526159dda86e
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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