Propargyl alcohol → HCID 14678437, compound

HRID 477755Notes

Reaction equation

HRID 477755 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:13]=2[C:14]([OH:16])=[O:15])[N:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:34](O)[C:35]#[CH:36].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:13]=2[C:14]([O:16][CH2:36][C:35]#[CH:34])=[O:15])[N:6]=1

Participants

7

Reactant 4

HCID 7859Propargyl alcoholHCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 4056919Benzoic acid, 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-6-fluoro-

Product 1

HCID 14678437HCID 14678437, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(4,6-dimethoxypyrimidin-2-yl)oxy-6-fluorobenzoic acid (3.0 g) and carbonyldiimidazole (1.8 g) was dissolved in tetrahydrofuran (50 ml), and the solution was refluxed under heating for one hour. The reaction solution was cooled. Then, propargyl alcohol (2.0 g) and potassium carbonate (1.7 g) were added thereto, and the mixture was refluxed under heating for one hour. The mixture was poured into water and extracted with ethyl ether. The extract was washed with water and dried. Then, the solvent was distilled off, and the residue thereby obtained was purified by silica gel column chromatography to obtain propargyl 2-(4,6-dimethoxypyrimidin-2-yl)oxy-6-fluorobenzoate (1.8 g). Yield: 53%, white crystals, Melting point: 49°-50° C.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for one hour
  3. temperatureThe reaction solution was cooled
  4. temperaturethe mixture was refluxed
  5. temperatureunder heating for one hour
  6. extractionextracted with ethyl ether
  7. washThe extract was washed with water
  8. customdried
  9. distillationThen, the solvent was distilled off
  10. customthe residue thereby obtained
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7d0fa281f387455abd263667ec4e7c44
Source dataset
uspto-grants-1989_12
Patent number
US04889552

Reaction notes

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