Potassium Carbonate → HCID 18979503, compound

HRID 2392591Notes

Reaction equation

HRID 2392591 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.Cl[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[OH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][O:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:12]=[O:13])=[CH:14][CH:15]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 900121-Octanol, 8-chloro-HCID 18979593HCID 18979593, compound

Product 1

HCID 18979503HCID 18979503, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 6.1 g of 4-(5-hydroxypyrimidin-2-yl)benzaldehyde and 6.0 g of 8-chloro-1-octanol in 100 ml of ethyl methyl ketone was treated with 16.9 g of finely powdered potassium carbonate and the mixture was heated under slight reflux overnight. The suspension was suction filtered and the filtrate was concentrated in a vacuum. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 1:1) gave 5.5 g of 4-(5-[8-hydroxyoctyloxy]-pyrimidin-2-yl)benzaldehyde.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder slight reflux overnight
  3. filtrationsuction filtered
  4. concentrationthe filtrate was concentrated in a vacuum

Sources & evidence

ORD record
ord-e879470b8ec14c3a902c022d20fe5fe1
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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