2-(2-(2-(Pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethyl methane sulfonate → 5-Octyloxy-2-[4-(2-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethoxy)phenyl]pyrimidine
Reaction equation
CS([O:5][CH2:6][CH2:7][O:8][CH2:9][C:10]([O:13][C:14]([F:27])([F:26])[C:15]([F:25])([F:24])[O:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])([F:12])[F:11])(=O)=O.[CH2:28]([O:36][C:37]1[CH:38]=[N:39][C:40]([C:43]2[CH:48]=[CH:47][C:46](O)=[CH:45][CH:44]=2)=[N:41][CH:42]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>>[CH2:28]([O:36][C:37]1[CH:42]=[N:41][C:40]([C:43]2[CH:48]=[CH:47][C:46]([O:5][CH2:6][CH2:7][O:8][CH2:9][C:10]([O:13][C:14]([F:27])([F:26])[C:15]([F:25])([F:24])[O:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])([F:12])[F:11])=[CH:45][CH:44]=2)=[N:39][CH:38]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]Participants
3
Procedure
The title compound was prepared essentially as in Example 1 by combining 2-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethyl methane sulfonate (4.54 g, 10 mmol, prepared from 2-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethanol and methanesulfonyl chloride) with 5-octyloxy-2-(4-hydroxyphenyl)pyrimidine (3.0 g, 10 mmol). The resulting crude product was purified by recrystallization from ethanol followed by Kugelrohr distillation (230° C. at 0.3 torr) to provide a yield of 6.5 g.
Workup
- customThe resulting crude product was purified by recrystallization from ethanol
- distillationfollowed by Kugelrohr distillation (230° C. at 0.3 torr)
- customto provide a yield of 6.5 g
Sources & evidence
- ORD record
- ord-236043c2e76e424cb0026e0cac098774
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05928562
Reaction notes
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