3,7-Dimethyl-2,6-octadienol → HCID 54555151, compound

HRID 372675Notes

Reaction equation

HRID 372675 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3][CH2:4][OH:5].[Na].Cl[C:14]1[NH:19][C:18](=[O:20])[C:17]([F:21])=[CH:16][N:15]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3][CH2:4][O:5][C:14]1[NH:19][C:18](=[O:20])[C:17]([F:21])=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 44583,7-Dimethyl-2,6-octadienolHCID 2553942-Chloro-5-fluoropyrimidin-4(3H)-oneHCID 5360545Sodium2×

Product 1

HCID 54555151HCID 54555151, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

23.1 g of 3,7-dimethyl-2,6-octadien-1-ol and 3.4 g of metal sodium are added to 200 ml of absolute toluene, and the mixture is stirred at 40° to 50° C until the metal sodium has been completely dissolved. Subsequently 7.4 g of 2-chloro-5-fluoropyrimidin-4-one is added to the solution, and the mixture is refluxed for 8 hours. The solvent is distilled off from the resulting reaction mixture, 30 ml of water is added to the residue and the pH of the mixture is adjusted to 4-5 with dilute hydrochloric acid. The resulting mixture is extracted with 200 ml of chloroform and the extract is concentrated. Purification of the residue by silica gel column chromatography gives 8.3 g of slightly yellow oily 2-(3,7-dimethyl-2,6-octadien-1-oxy)-5-fluoropyrimidin-4-one in a yield of 61.0%.

Workup

  1. dissolutionhas been completely dissolved
  2. temperaturethe mixture is refluxed for 8 hours
  3. distillationThe solvent is distilled off from the resulting reaction mixture, 30 ml of water
  4. additionis added to the residue
  5. extractionThe resulting mixture is extracted with 200 ml of chloroform
  6. concentrationthe extract is concentrated
  7. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-4c7590f9682f430995914ed350420936
Source dataset
uspto-grants-1978_05
Patent number
US04092313

Reaction notes

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