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5-Octyl-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine → 5-Hexyloxy-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

HRID 2257475
Notes
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Reaction equation

HRID 2257475 reaction equation
C(C1C=NC(C2C=CC(O[CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]([O:30][C:31]([F:48])([F:47])[C:32]([F:46])([F:45])[O:33][C:34]([F:44])([F:43])[C:35]([F:42])([F:41])[O:36][C:37]([F:40])([F:39])[F:38])([F:29])[F:28])=CC=2)=NC=1)CCCCCCC.[CH2:49]([O:55][C:56]1[CH:57]=[N:58][C:59]([C:62]2[CH:67]=[CH:66][C:65]([OH:68])=[CH:64][CH:63]=2)=[N:60][CH:61]=1)[CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]>O>[CH2:49]([O:55][C:56]1[CH:61]=[N:60][C:59]([C:62]2[CH:63]=[CH:64][C:65]([O:68][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]([O:30][C:31]([F:47])([F:48])[C:32]([F:45])([F:46])[O:33][C:34]([F:43])([F:44])[C:35]([F:41])([F:42])[O:36][C:37]([F:40])([F:39])[F:38])([F:29])[F:28])=[CH:66][CH:67]=2)=[N:58][CH:57]=1)[CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 212253045-Octyl-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidineHCID 1361744305-Hexyloxy-2-(4-hydroxyphenyl)pyrimidine

Product 1

HCID 212253595-Hexyloxy-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

The title compound was prepared essentially as in Example 1 by combining 3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-chloropropane (5.42 g, 11.4 mmol, Example 24) with 5-hexyloxy-2-(4-hydroxyphenyl)pyrimidine (3 g, 10.0 mmol). Product was isolated by addition of water (100 mL) to the resulting mixture, followed by filtration and recrystallization from ethanol. The recrystallized precipitate was dried at about 130° C., and the resulting product was further purified by Kugelrohr distillation (b.p. 170°-180° C. at 2.0 torr; yield of 5.4 g).

Workup

  1. filtrationfollowed by filtration and recrystallization from ethanol
  2. customThe recrystallized precipitate was dried at about 130° C.
  3. distillationthe resulting product was further purified by Kugelrohr distillation (b.p. 170°-180° C. at 2.0 torr; yield of 5.4 g)

Sources & evidence

ORD record
ord-7646d047c4f94447907379ec1ca0776c
Source dataset
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05658491

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes