Diisopropylamine → 1-(Phenylsulfanyl)-4-pyridin-3-ylbutan-2-ol

HRID 1935713Notes

Reaction equation

HRID 1935713 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[CH2:20]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:21]1[O:23][CH2:22]1>O1CCCC1.O>[C:25]1([S:24][CH2:20][CH:21]([OH:23])[CH2:22][CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 79703-MethylpyridineHCID 110949982-((Phenylsulfanyl)methyl)oxiraneHCID 178418339Butyllithium

Product 1

HCID 224653391-(Phenylsulfanyl)-4-pyridin-3-ylbutan-2-olYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Under argon gas, a solution of diisopropylamine (0.835 g, 8.25 mmol) in tetrahydrofuran (5 mL) was added dropwise to n-butyllithium (1.53 M in hexane, 4.9 mL, 7.5 mmol) at 5° C. and the mixture was stirred for 30 minutes. To this was further added a solution of 3-methylpyridine (1.40 g, 15 mmol) in tetrahydrofuran (5 mL) dropwise at 5° C., and the mixture was stirred for 30 minutes. Then, a solution of phenyl glycidyl thioether (0.83 g, 5 mmol) in tetrahydrofuran (5 mL) was added at 5° C. and the reaction was carried out for 2 hours. This reaction mixture was diluted with 10 mL of water for hydrolysis, and extracted with 20 mL of ethyl acetate. The organic layer was washed with 10 mL of water twice and the solvent was distilled off under reduced pressure to give a deep-red oil. This oil was purified by silica gel column chromatography (Merck's Kieselgel 60, hexane/ethyl acetate=1/2) to give 0.521 g (isolation yield: 41%) of 1-(phenylsulfanyl)-4-pyridin-3-ylbutan-2-ol (yellow oil).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. waitthe reaction was carried out for 2 hours
  3. extractionextracted with 20 mL of ethyl acetate
  4. washThe organic layer was washed with 10 mL of water twice
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto give a deep-red oil
  7. customThis oil was purified by silica gel column chromatography (Merck's Kieselgel 60, hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-4cb8ed3250244702955dba06983023f7
Source dataset
uspto-grants-2002_05
Patent number
US06388086B1

Reaction notes

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