Methyl Ethyl Ketone → HCID 178442733, compound

HRID 2254990Notes

Reaction equation

HRID 2254990 reaction equation
[CH2:1]([C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH2:23]([C@H:28]1[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH2:36]Br)[CH2:30][CH2:29]1)[CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:23]([C@H:28]1[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH2:36][O:22][C:19]2[CH:18]=[CH:17][C:16]([C:13]3[N:14]=[CH:15][C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:11][N:12]=3)=[CH:21][CH:20]=2)[CH2:30][CH2:29]1)[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 1358247454-(5-Nonyl-2-pyrimidinyl)phenolHCID 178444432HCID 178444432, compound

Product 1

HCID 178442733HCID 178442733, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.5 g of 4-(5-nonyl-2-pyrimidinyl)phenol, 0.55 g of 3-(trans-4-pentylcyclohexyl)-1-propyl bromide, 0.91 g of potassium carbonate and 50 ml of absolute butanone was heated under reflux overnight. Subsequently, the cooled reaction mixture was poured into water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed with 500 ml of water, dried over magnesium sulfate, filtered and concentrated. Chromatography of the residue on silica gel with toluene and recrystallization from ethanol gave pure 2-(4-[3-(trans-4-pentylcyclohexyl)-1-propyloxy]phenyl-5-nonylpyrimidine with m.p. (C--SC) 83° C., transition SC --N 103° C., cl.p. (N-I) 133° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customSubsequently, the cooled reaction mixture
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. washThe combined organic phases were washed with 500 ml of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatography of the residue on silica gel with toluene and recrystallization from ethanol

Sources & evidence

ORD record
ord-d59058daa1b040928ee32393a963900f
Source dataset
uspto-grants-1993_08
Patent number
US05238600

Reaction notes

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