Sodium borohydride → 4-[2-(4-Methoxyphenyl)-2-hydroxyethylthiomethyl]pyridine

HRID 485060Notes

Reaction equation

HRID 485060 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][S:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[O:11])=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]([OH:11])[CH2:9][S:8][CH2:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13490317alpha(4-Picolylthio)-p-methoxyacetophenone

Product 1

HCID 202712734-[2-(4-Methoxyphenyl)-2-hydroxyethylthiomethyl]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, alpha-(4-picolylthio)p-methoxyacetophenone (1.99 g., 7.3 mmoles) was dissolved in 25 ml. of stirring ethanol. Sodium borohydride (0.45 g., 11.7 mmoles) was added portionwise and the mixture then refluxed gently for 30 minutes. The mixture was partially cooled and evaporated to dryness. Water (50 ml.) was added to the residue, which was then acidified with excess 1N hydrochloric acid. The acid solution was made basic with solid sodium bicarbonate and product extracted into ethyl acetate. The ethyl acetate was dried over anhydrous sodium sulfate and concentrated to an oil, which crystallized on standing. Trituration with diethyl ether and filtration gave purified 4-[2-(4-methoxyphenyl)-2-hydroxyethylthiomethyl]pyridine (1.50 g.; m.p. 70°-72.5° C.; pnmr/CDCl3 /TMS/delta: 7.2 (d, 2H), 6.4 (s, 2H), 6.3 (1H, exchanges with D2O), 6.2 (d, 3H), 5.3 (t, 1H), 3.2 (broad doublet, 2H), 2.7 (d and s, 4H), 1.5 (d, 2H); ir (KBr): 3.25, 6.25, 6.65, 8.05, 8.6, 12.5μ].

Workup

  1. temperaturethe mixture then refluxed gently for 30 minutes
  2. temperatureThe mixture was partially cooled
  3. customevaporated to dryness
  4. additionWater (50 ml.) was added to the residue, which
  5. extractionextracted into ethyl acetate
  6. dry with materialThe ethyl acetate was dried over anhydrous sodium sulfate
  7. concentrationconcentrated to an oil, which
  8. customcrystallized
  9. filtrationTrituration with diethyl ether and filtration
  10. customgave
  11. custompurified 4-[2-(4-methoxyphenyl)-2-hydroxyethylthiomethyl]pyridine (1.50 g

Sources & evidence

ORD record
ord-b34f022687f74621b5f3f889ce752550
Source dataset
uspto-grants-1985_08
Patent number
US04535084

Reaction notes

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