Water → (+)-5-Octyl-2-[4-(2-fluoroheptyloxy)phenyl]pyrimidine

HRID 2379659Notes

Reaction equation

HRID 2379659 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]([F:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=O)=O)=CC=1.[CH2:20]([C:28]1[CH:29]=[N:30][C:31]([C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)=[N:32][CH:33]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[OH-].[Na+].O>C(O)CCC>[CH2:20]([C:28]1[CH:33]=[N:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:11][CH:12]([F:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:36][CH:35]=2)=[N:30][CH:29]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 14716844(+)-2-Fluoroheptyl p-toluenesulfonate

Product 1

HCID 14597237(+)-5-Octyl-2-[4-(2-fluoroheptyloxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

0.43 g (1.5 mmol) of the thus obtained (+)-2-fluoroheptyl p-toluenesulfonate and 0.28 g (1.0 mmol) of 5-octyl-2-(4-hydroxyphenyl)pyrimidine were mixed with 0.2 ml of 1-butanol, followed by sufficient stirring. To the solution was quickly added a previously obtained alkaline solution of 0.048 g (1.2 mmol) of sodium hydroxide in 1.0 ml of 1-butanol, followed by 5.5 hours of heat-refluxing. After the reaction, 10 ml of distilled water was added, and the mixture was extracted respectively once with 10 ml of benzene and 5 ml of benzene, followed by drying with an appropriate amount of anhydrous sodium sulfate, distilling-off of the solvent and purification by silica gel column chromatography (chloroform) to obtain 0.17 g (0.43 mmol) of objective (+)-5-octyl-2-[4-(2-fluoroheptyloxy)phenyl]pyrimidine.

Workup

  1. temperatureof heat-refluxing
  2. additionwas added
  3. extractionthe mixture was extracted respectively once with 10 ml of benzene and 5 ml of benzene
  4. dry with materialby drying with an appropriate amount of anhydrous sodium sulfate, distilling-off of the solvent and purification by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-963b9dd530424a6fa647626e6423201b
Source dataset
uspto-grants-1994_11
Patent number
US05364559

Reaction notes

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