Hydrochloric Acid → 3-[p-[3-(2-Hydroxyethyl)oxy-2-methylpropionyl]benzyl]pyridine

HRID 986442Notes

Reaction equation

HRID 986442 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].CN(C)C=[O:10].Cl[CH2:13][CH:14]([CH3:30])[C:15]([C:17]1[CH:29]=[CH:28][C:20]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:19][CH:18]=1)=[O:16].Cl>C(O)CO.O>[OH:4][CH2:2][CH2:5][O:10][CH2:13][CH:14]([CH3:30])[C:15]([C:17]1[CH:29]=[CH:28][C:20]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:19][CH:18]=1)=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 137455203-[p-(3-Chloro-2-methylpropionyl)benzyl]pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 137455213-[p-[3-(2-Hydroxyethyl)oxy-2-methylpropionyl]benzyl]pyridineYield 85.8%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

In 50 ml of ethylene glycol was dissolved 5.0 g of potassium tert-butoxide, and a mixture solution of 6 ml of N,N-dimethylformamide and 5.0 g of 3-[p-(3-chloro-2-methylpropionyl)benzyl]pyridine was added in small portions to the above solution with ice-cooling, after which the resulting mixture was subjected to reaction at the same temperature for 2 hours, and then neutralized with 9 ml of 2N hydrochloride acid and diluted with 50 ml of water. The resulting mixture was extracted with two 50-ml portions of methylene chloride. 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 (1:3 by volume)] to obtain 5.63 g (yield 85.8%) of colorless, oily 3-[p-[3-(2-hydroxyethyl)oxy-2-methylpropionyl]benzyl]pyridine.

Workup

  1. temperaturecooling
  2. customafter which the resulting mixture was subjected to reaction at the same temperature for 2 hours
  3. extractionThe resulting mixture was extracted with two 50-ml portions of methylene chloride
  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 (1:3 by volume)]

Sources & evidence

ORD record
ord-00357881a9ea40dd8d77b5eb44647297
Source dataset
uspto-grants-1987_12
Patent number
US04713387

Reaction notes

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