Potassium Hydroxide → (S)-5-(8-methyldecyloxy)-2-(4-octyloxyphenyl)pyrimidine

HRID 330222Notes

Reaction equation

HRID 330222 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:5]=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:11]=2)=[N:8][CH:9]=1.[CH3:25][C@@H:26]([CH2:35][CH3:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br>C(O)C>[CH3:25][C@@H:26]([CH2:35][CH3:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:3][C:4]1[CH:5]=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:11]=2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 144963952-(4-(Octyloxy)phenyl)pyrimidin-5-olHCID 14496397(S)-8-methyldecyl bromide

Product 1

HCID 14496399(S)-5-(8-methyldecyloxy)-2-(4-octyloxyphenyl)pyrimidineYield 29.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

KOH (0.8 g) was added to a solution of 5-hydroxy-2-(4-octyloxyphenyl)pyrimidine (4 g) dissolved in ethanol (20 ml), followed by adding (S)-8-methyldecyl bromide (3.2 g) prepared according to the method disclosed in the literature (Mol. Cryst. Liq. Cryst., 1984, Vol. 114, pp. 237-247), keeping the mixture under reflux for 6 hours, allowing the resulting material to cool down, extracting it with toluene, washing the resulting organic layer with 2N-NaOH aqueous solution, further washing with water until the washing water became neutral, distilling off low-boiling components in the organic layer and recrystallizing the residue from ethanol to obtain the captioned compound, (S)-5-(8-methyldecyloxy)-2-(4-octyloxyphenyl)pyrimidine (1.8 g). Its phase transition points were as follows: ##STR12##

Workup

  1. customprepared
  2. temperatureunder reflux for 6 hours
  3. temperatureto cool down
  4. extractionextracting it with toluene
  5. washwashing the resulting organic layer with 2N-NaOH aqueous solution
  6. washfurther washing with water until the washing water
  7. distillationdistilling off low-boiling components in the organic layer
  8. customrecrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-c6406eb115c34adbb01cf521c9a59aec
Source dataset
uspto-grants-1990_01
Patent number
US04895671

Reaction notes

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