1,1,1-Trifluoro-2-propanol → HCID 58413253, compound

HRID 532264Notes

Reaction equation

HRID 532264 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3]([OH:5])[CH3:4].[H-].[Li+].F[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1>C1COCC1>[N+:17]([C:16]1[C:11]([O:5][CH:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[N:12][CH:13]=[CH:14][CH:15]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 97741,1,1-Trifluoro-2-propanolHCID 62714Lithium hydrideHCID 27628172-Fluoro-3-nitropyridine

Product 1

HCID 58413253HCID 58413253, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

1,1,1-Trifluoro-2-propanol (3.2 g) was dissolved in THF (4.0 ml) and cooled to 0° C. Then LiH MDS (1M in THF; 28.3 ml) was added dropwise. The reaction mixture was stirred at 0° C. for 20 minutes. A solution of 2-fluoro-3-nitro-pyridine (4.0 g) in THF (1 ml) was added and the mixture was stirred overnight. It was quenched by addition of saturated NH4Cl solution and extracted with dichloromethane. The organic layer was dried and concentrated in vacuo.

Workup

  1. stirringthe mixture was stirred overnight
  2. customIt was quenched by addition of saturated NH4Cl solution
  3. extractionextracted with dichloromethane
  4. customThe organic layer was dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8798ba504a449f5880237ad438270b1
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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