Potassium Carbonate → HCID 18645076, compound

HRID 2050420Notes

Reaction equation

HRID 2050420 reaction equation
[CH3:1][C@@H:2]([CH2:20][CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=2)=[N:11][CH:12]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:1][C@@H:2]([CH2:20][CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:25][CH2:22][CH2:12][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH:20]=[CH2:21])=[CH:15][CH:14]=2)=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 136341178HCID 136341178, compound

Product 1

HCID 18645076HCID 18645076, compoundYield 242.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 0.66 g of 9-decen-1-yl-p-tosylate, 0.5 g of (S)-4-(5-[5-methylheptyl]-2-pyrimidinyl)phenol and 0.97 g of potassium carbonate and 50 ml of absolute butanone was heated under reflux overnight. The cooled reaction mixture was subsequently poured into ice-water and extracted three times with 50 ml of diethyl ether each time. The organic phases were washed with 500 ml of water, dried over magnesium sulphate and concentrated. Chromatography of the residue on silica gel with toluene and subsequent bulb-tube distillation gave 0.9 g of (S)-5-(5-methylheptyl)-2-(4-[9 -decenyloxy]phenyl)pyrimidine; m.p. (C-SC *) 19° C., phase transition (SC *-Ch) 32.5° C., cl.p. (Ch-I) 43° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe cooled reaction mixture
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. washThe organic phases were washed with 500 ml of water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. distillationChromatography of the residue on silica gel with toluene and subsequent bulb-tube distillation

Sources & evidence

ORD record
ord-99a3f35d7adb40aa8d744536d73a18b7
Source dataset
uspto-grants-1991_05
Patent number
US05013476

Reaction notes

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