Methyl iodide → HCID 22880427, compound

HRID 1941057Notes

Reaction equation

HRID 1941057 reaction equation
[CH3:1]I.[CH2:3]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C@H:25]([OH:53])[CH2:26][O:27][CH2:28][C:29]([O:32][C:33]([F:52])([F:51])[C:34]([F:50])([F:49])[O:35][C:36]([F:48])([F:47])[C:37]([F:46])([F:45])[C:38]([F:44])([F:43])[C:39]([F:42])([F:41])[F:40])([F:31])[F:30])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Na+]>CN(C)C=O.O>[CH2:3]([C:11]1[CH:16]=[N:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][C@H:25]([O:53][CH3:1])[CH2:26][O:27][CH2:28][C:29]([O:32][C:33]([F:52])([F:51])[C:34]([F:49])([F:50])[O:35][C:36]([F:47])([F:48])[C:37]([F:45])([F:46])[C:38]([F:43])([F:44])[C:39]([F:40])([F:41])[F:42])([F:30])[F:31])=[CH:21][CH:22]=2)=[N:13][CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10941720HCID 10941720, compound

Product 1

HCID 22880427HCID 22880427, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (1.1 g, 7.76 mmol) was added to a solution of 5-octyl-2-[4-((R)-2-hydroxy-3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2,-difluoroethoxy)propoxy)phenyl]pyrimidine (Example 4, 1.5 g, 1.94 mmol) and sodium hydride (116 mg, 60 weight percent in oil, 2.91 mmol) in dimethyl formamide (10 ml). The resulting mixture was stirred at room temperature for 10 hours, was diluted with 50 ml of water, and was extracted with three 50 ml aliquots of diethyl ether. The organic extracts were dried (over MgSO4), filtered, and concentrated. The resulting product was then recrystallized from methanol at -30° C. to give a white smectic material.

Workup

  1. extractionwas extracted with three 50 ml aliquots of diethyl ether
  2. dry with materialThe organic extracts were dried (over MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting product was then recrystallized from methanol at -30° C.
  6. customto give a white smectic material

Sources & evidence

ORD record
ord-d8ce50cc400340f3b443b0e9745fe419
Source dataset
uspto-grants-1997_12
Patent number
US05702637

Reaction notes

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