2,2,2-Trifluoroethanol → HCID 23128080, compound

HRID 358681Notes

Reaction equation

HRID 358681 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[CH2:9]([O:12][C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][C:18](F)=[CH:19][CH:20]=2)[N:15]([CH3:25])[CH:14]=1)[CH:10]=[CH2:11]>O1CCOCC1>[CH2:9]([O:12][C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][C:18]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[CH:19][CH:20]=2)[N:15]([CH3:25])[CH:14]=1)[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 23128086HCID 23128086, compound

Product 1

HCID 23128080HCID 23128080, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,2,2-Trifluoroethanol (7.0 ml) was added to a stirred suspension of sodium hydride (4.0 g of a 50% dispersion in mineral oil) in dioxan (60 ml). After 30 minutes 3-allyloxy-7-fluoro-1-methyl-4-quinolone (2.8 g) was added and the mixture heated under reflux for 24 hours. The solvent was removed by evaporation under reduced pressure at 40°. The residue was dissolved in water (150 ml) and the solution extracted with dichloromethane (3×150 ml). The combined extracts were dried over magnesium sulphate and evaporated to give the novel compound 3-allyloxy-1-methyl-7-(2,2,2-trifluoroethoxy)-4-quinolone, m.p. 120°.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent was removed by evaporation under reduced pressure at 40°
  4. dissolutionThe residue was dissolved in water (150 ml)
  5. extractionthe solution extracted with dichloromethane (3×150 ml)
  6. dry with materialThe combined extracts were dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-b408aace7ea54c2ea61b5deb42c8a217
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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