Acetic Acid → 3-[p-(3-Chloro-1-hydroxy-2-methylpropyl)benzyl]pyridine

HRID 986447Notes

Reaction equation

HRID 986447 reaction equation
[Cl:1][CH2:2][CH:3]([CH3:19])[C:4]([C:6]1[CH:18]=[CH:17][C:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)=[O:5].B.[Na].C(O)(=O)C.[Cl-].[Na+]>C(O)C>[Cl:1][CH2:2][CH:3]([CH3:19])[CH:4]([C:6]1[CH:18]=[CH:17][C:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)[OH:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 137455203-[p-(3-Chloro-2-methylpropionyl)benzyl]pyridineHCID 178418435HCID 178418435, compound

Product 1

HCID 201486153-[p-(3-Chloro-1-hydroxy-2-methylpropyl)benzyl]pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 17 ml of ethanol was dissolved 2.28 g of 3-[p-(3-chloro-2-methylpropionyl)benzyl]pyridine, and to the resulting solution was added 0.3 g of sodium boron hydride in small portions with ice-cooling, after which the resulting mixture was subjected to reaction at the same temperature for one hour. To the reaction mixture were added successively 0.54 ml of acetic acid and 30 ml of a saturated aqueous sodium chloride solution, and the resulting mixture was extracted with two 20-ml portions of ethyl acetate. The extracts were combined, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform:ethyl acetate (1:1 by volume)] to obtain 2.29 g (yield 99.0%) of colorless, oily 3-[p-(3-chloro-1-hydroxy-2-methylpropyl)benzyl]pyridine.

Workup

  1. temperaturecooling
  2. customafter which the resulting mixture was subjected to reaction at the same temperature for one hour
  3. extractionthe resulting mixture was extracted with two 20-ml portions of ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform:ethyl acetate (1:1 by volume)]

Sources & evidence

ORD record
ord-9c1824b76cde4f0984467d58d410a8d8
Source dataset
uspto-grants-1987_12
Patent number
US04713387

Reaction notes

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