1,1,1-Trifluoro-2-propanol → HCID 66787555, compound

HRID 2381161Notes

Reaction equation

HRID 2381161 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]([F:17])([F:16])[CH:13]([OH:15])[CH3:14].[H-].[Na+]>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:15][CH:13]([CH3:14])[C:12]([F:17])([F:16])[F:11])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 97741,1,1-Trifluoro-2-propanolHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 66787555HCID 66787555, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-nitro-pyridine (1.74 g) and 1,1,1-trifluoro-propan-2-ol (1.097 g) in DMF (15 ml) under an argon atmosphere was added under ice cooling NaH (0.528 g, 55% suspension in oil). The mixture was stirred for 3 h at RT then partitioned between diethyl ether and water, the layers were separated dried over Na2SO4 and the solvent was evaporated off to give (rac)-5-nitro-2-(2,2,2-trifluoro-1-methyl-ethoxy)-pyridine as brown oil (2.28 g) that was used in the next step without further purification.

Workup

  1. customthen partitioned between diethyl ether and water
  2. customthe layers were separated
  3. dry with materialdried over Na2SO4
  4. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-e4a608f93665478abe584f6eb0d667a0
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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