Hydrochloric Acid → 3-[p-[1-Hydroxy-3-(2-hydroxyethyl)oxy-2-methylpropyl]benzyl]pyridine

HRID 569162Notes

Reaction equation

HRID 569162 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([CH3:22])[C:7]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)=[O:8].B.[Na].Cl>C(O)C>[OH:8][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:20][CH:21]=1)[CH:6]([CH3:22])[CH2:5][O:4][CH2:3][CH2:2][OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 137455213-[p-[3-(2-Hydroxyethyl)oxy-2-methylpropionyl]benzyl]pyridineHCID 178418435HCID 178418435, compound

Product 1

HCID 201486043-[p-[1-Hydroxy-3-(2-hydroxyethyl)oxy-2-methylpropyl]benzyl]pyridineYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 22.5 ml of ethanol was dissolved 4.51 g of 3-[p-[3-(2-hydroxyethyl)oxy-2-methylpropionyl]benzyl]pyridine, and 286 mg of sodium boron hydride was added in small portions to the resulting solution with ice-cooling, after which the resulting mixture was subjected to reaction at the same temperature for one hour. The solvent was removed by distillation under reduced pressure, and 22.5 ml of water and 22.5 ml of ethyl acetate were added to the residue thus obtained, after which the pH thereof was adjusted to 7.0 with 2N hydrochloric acid. The organic layer was separated, washed with 10 ml of water, and 22.5 ml of water was added to the organic layer, after which the pH thereof was adjusted to 1.5 with 2N hydrochloric acid. The aqueous layer was separated, and then washed with 10 ml of ethyl acetate, after which 22.5 ml of ethyl acetate was added to the aqueous layer. The resulting mixture was neutralized with sodium hydrogencarbonate. The organic layer was separated, washed with 10 ml of water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 4.2 g (yield 92.5%) of colorless, oily 3-[p-[1-hydroxy-3-(2-hydroxyethyl)oxy-2-methylpropyl]benzyl]pyridine.

Workup

  1. additionwas added in small portions to the resulting solution with ice-
  2. temperaturecooling
  3. customafter which the resulting mixture was subjected to reaction at the same temperature for one hour
  4. customThe solvent was removed by distillation under reduced pressure, and 22.5 ml of water and 22.5 ml of ethyl acetate
  5. additionwere added to the residue
  6. customthus obtained
  7. customThe organic layer was separated
  8. washwashed with 10 ml of water, and 22.5 ml of water
  9. additionwas added to the organic layer
  10. customThe aqueous layer was separated
  11. washwashed with 10 ml of ethyl acetate
  12. additionafter which 22.5 ml of ethyl acetate was added to the aqueous layer
  13. customThe organic layer was separated
  14. washwashed with 10 ml of water
  15. dry with materialdried over anhydrous magnesium sulfate
  16. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f1775a7f615442cbb600d65a4e293a0e
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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