Methyl Acetate → 3-[p-(3-Acetoxy-1-chloro-2-methylpropyl)benzyl]pyridine

HRID 569177Notes

Reaction equation

HRID 569177 reaction equation
[C:1]([O:4][CH2:5][CH:6]([CH3:22])[CH: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)(=[O:3])[CH3:2].S(Cl)([Cl:25])=O.C(OC)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[C:1]([O:4][CH2:5][CH:6]([CH3:22])[CH: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)[Cl:25])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6584Methyl AcetateHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 201486363-[p-(3-Acetoxy-1-hydroxy-2-methylpropyl)benzyl]pyridine

Product 1

HCID 137455283-[p-(3-Acetoxy-1-chloro-2-methylpropyl)benzyl]pyridineYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In 4.6 ml of methylene chloride was dissolved 910 mg of 3-[p-(3-acetoxy-1-hydroxy-2-methylpropyl)benzyl]pyridine, and to the resulting solution was added 0.48 ml of thionyl chloride with ice-cooling, after which the resulting mixture was subjected to reaction at the same temperature for one hour. The solvent and the excessive thionyl chloride were removed by distillation under reduced pressure, and to the residue thus obtained were added 10 ml of methyl acetate and 10 ml of water, after which the resulting mixture was neutralized with sodium hydrogencarbonate. The organic layer was separated, washed with 5 ml of 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: benzene:ethyl acetate (5:1 by volume)] to obtain 740 mg (yield 86.0%) of colorless, oily 3-[p-(3-acetoxy-1-chloro-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. customThe solvent and the excessive thionyl chloride were removed by distillation under reduced pressure
  4. customto the residue thus obtained
  5. customThe organic layer was separated
  6. washwashed with 5 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue thus obtained
  10. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (5:1 by volume)]

Sources & evidence

ORD record
ord-7962bbd87b844780b3401364221aeb4e
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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