Isopropanol → HCID 66996496, compound

HRID 623815Notes

Reaction equation

HRID 623815 reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:6])[CH3:5].Cl[C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:15]=1)[C:11]#[N:12]>C1COCC1.C(OCC)(=O)C>[CH:4]([O:6][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([C:16]([F:19])([F:17])[F:18])[N:15]=1)[C:11]#[N:12])([CH3:5])[CH3:3]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 534076042-Chloro-6-(trifluoromethyl)pyridine-4-carbonitrile

Product 1

HCID 66996496HCID 66996496, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

In a 250-ml capacity 3 neck flask (1.39 g) NaH suspended in 100 ml THF. At 0° C. IPA (4.36 g) in 20 ml THF added in this reaction flask. Allow it to stir at RT for 3 h. At 0° C. 2-chloro-6-trifluoromethylisonicotinonitrile (10 g) in 80 mL THF added in the flask in dropwise manner. Maintained 0° C. temperature for 30 min. Completion of reaction conformed by TLC. Reaction mixture was dumped in ice water. Extract compound in ethyl acetate. Organic layer was washed by water two times & dried over Na2SO4, filtered, and concentrated by rotary evaporation (40° C., 20 mmHg) to afford 8 g of yellow oil. The resulting crude compound forwarded for next step.

Workup

  1. customAt 0° C
  2. customAt 0° C
  3. temperatureMaintained 0° C. temperature for 30 min
  4. customCompletion of reaction
  5. customReaction mixture
  6. washOrganic layer was washed by water two times
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation (40° C., 20 mmHg)

Sources & evidence

ORD record
ord-788aaacee2bc4fcdb1af64ff82efed22
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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