Triethylamine → 1-Methyl-2-benzyloxyethyl 2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionate
Reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:20][C:21]1[C:22]([O:28][C:29]2[CH:40]=[CH:39][C:32]([O:33][CH:34]([CH3:38])[C:35](Cl)=[O:36])=[CH:31][CH:30]=2)=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=1>C1(C)C=CC=CC=1>[Cl:20][C:21]1[C:22]([O:28][C:29]2[CH:40]=[CH:39][C:32]([O:33][CH:34]([CH3:38])[C:35]([O:12][CH:10]([CH3:11])[CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:36])=[CH:31][CH:30]=2)=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
16.6 g of 1-benzyloxy-2-propanol and 10.6 g of triethylamine were dissolved in 200 ml of toluene, then cooled to 0° C. To this solution was dropwise added a solution of 34.7 g of 2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionyl chloride in 80 ml of toluene at 0° to 5° C. with stirring. After the dropwise addition, the mixture was gradually heated and, at 40° to 50° C., it was stirred for one hour to complete the reaction. After cooling to room temperature, it was washed successively with 1% strength by weight sodium hydroxide aqueous solution and water, followed by drying. Upon distilling off toluene under reduced pressure, there were obtained 43.3 g of pale yellow, viscous, oily 1-methyl-2-benzyloxyethyl 2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionate. nD20 1.5710.
Workup
- additionAfter the dropwise addition
- temperaturethe mixture was gradually heated and, at 40° to 50° C.
- stirringit was stirred for one hour
- customthe reaction
- temperatureAfter cooling to room temperature
- washit was washed successively with 1% strength by weight sodium hydroxide aqueous solution and water
- customby drying
- distillationUpon distilling off toluene under reduced pressure
Sources & evidence
- ORD record
- ord-6ac13698fa444f778ba631a572231c6e
- Source dataset
- uspto-grants-1984_04
- Patent number
- US04441913
Reaction notes
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