Hydrochloric Acid → HCID 118307048, compound

HRID 921189Notes

Reaction equation

HRID 921189 reaction equation
F[C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:13][C:14]([F:21])([F:20])[CH:15]([OH:19])[CH2:16][CH:17]=[CH2:18].[H-].[Na+].Cl>O1CCOCC1>[F:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:19][CH:15]([CH2:16][CH:17]=[CH2:18])[C:14]([F:21])([F:20])[F:13])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2782897Methyl 2,4-DifluorobenzoateHCID 109096421,1,1-trifluoro-4-penten-2-ol

Product 1

HCID 118307048HCID 118307048, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 2,4-difluorobenzoate (1.72 g, 9.99 mmol) was dissolved in dioxane. To this was added 1,1,1-trifluoropent-4-en-2-ol (1.40 g, 9.99 mmol) followed by 60% (mineral oil) NaH (0.40 g, 9.99 mmol). The resulting mixture was heated to 90° C. and stirred overnight. After cooling to RT, 1N HCl was added and the mixture transferred to separatory funnel. The mixture was extracted with ethyl acetate after which the organic solution was washed with 1N NaOH (2 times) and sat'd NaCl. The solution was dried over Na2SO4, filtered and the solvent removed to yield the title compound as an oil which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling to RT
  2. customthe mixture transferred to separatory funnel
  3. extractionThe mixture was extracted with ethyl acetate after which the organic solution
  4. washwas washed with 1N NaOH (2 times)
  5. dry with materialThe solution was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed

Sources & evidence

ORD record
ord-c604dcd325314d8a94d5513675110cf8
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

Loading…