Acetic Anhydride → 3-[p-[3-(2-Acetoxyethyl)oxy-2-methylpropionyl]benzyl]pyridine
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].[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1.C(OCC)(=O)C>[C:23]([O: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])(=[O:25])[CH3:24]Participants
5
Procedure
In 3 ml of pyridine was dissolved 2.0 g of 3-[p-[3-(2-hydroxyethyl)oxy-2-methylpropionyl]benzyl]pyridine, and 0.76 ml of acetic anhydride was added to the resulting solution with ice-cooling, after which the resulting mixture was subjected to reaction at room temperature for 12 hours. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was dissolved in 16 ml of ethyl acetate. The resulting solution was washed with 5 ml of water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain crude oily 3-[p-[3-(2-acetoxyethyl)oxy-2-methylpropionyl]benzyl]pyridine. This was dissolved in 17 ml of ethanol.
Workup
- additionwas added to the resulting solution with ice-
- temperaturecooling
- customafter which the resulting mixture was subjected to reaction at room temperature for 12 hours
- customThe solvent was removed by distillation under reduced pressure
- customthe residue thus obtained
- washThe resulting solution was washed with 5 ml of water
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-7ef5a5dfd8af47d1a9d5356901b249ee
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04731370
Reaction notes
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