Acetic Acid → 3-[p-(1-Chloro-3-hydroxy-2-methylpropyl)benzyl]pyridine
Reaction equation
C([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:8])(=O)C.C[O-].[Na+].C(O)(=O)C>CO.C(OCC)(=O)C>[Cl:8][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)[CH:6]([CH3:22])[CH2:5][OH:4]Participants
Procedure
In 10 ml of methanol was dissolved 740 mg of 3-[p-(3-acetoxy-1-chloro-2-methylpropyl)benzyl]pyridine, and to the resulting solution was added 40 mg of sodium methoxide with ice-cooling, after which the resulting mixture was subjected to reaction at room temperature for 30 minutes. To the reaction mixture was added 0.1 ml of acetic acid, and the solvent was removed by distillation under reduced pressure, after which the residue thus obtained was dissolved in 10 ml of ethyl acetate. The resulting solution was washed with 5 ml of water and then dried over anhydrous magnesium sulfate. The residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (1:1 by volume)] to obtain 400 mg (yield 62.3%) of colorless, oily 3-[p-(1-chloro-3-hydroxy-2-methylpropyl)benzyl]pyridine.
Workup
- temperaturecooling
- customafter which the resulting mixture was subjected to reaction at room temperature for 30 minutes
- customthe solvent was removed by distillation under reduced pressure
- customafter which the residue thus obtained
- washThe resulting solution was washed with 5 ml of water
- dry with materialdried over anhydrous magnesium sulfate
- customThe residue thus obtained
- customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (1:1 by volume)]
Sources & evidence
- ORD record
- ord-01dda6a01dee44e8aaf3271c4df0bec6
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04731370
Reaction notes
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