1,1,1,3,3,3-Hexafluoro-2-propanol → HCID 58042361, compound

HRID 512067Notes

Reaction equation

HRID 512067 reaction equation
[F:1][C:2]([F:10])([F:9])[CH:3]([OH:8])[C:4]([F:7])([F:6])[F:5].[H-].[Na+].Cl[C:14]1[C:19]([Cl:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N:15]=1>C1COCC1>[Cl:20][C:19]1[C:14]([O:8][CH:3]([C:4]([F:7])([F:6])[F:5])[C:2]([F:10])([F:9])[F:1])=[N:15][CH:16]=[C:17]([N+:21]([O-:23])=[O:22])[CH:18]=1

Participants

5

Reactant 3

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 24758Sodium hydrideHCID 27631062,3-Dichloro-5-nitropyridine

Product 1

HCID 58042361HCID 58042361, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1,1,3,3,3-Hexafluoropropan-2-ol (1.74 g, 10.35 mmol) was added to a suspension of sodium hydride in mineral oil (60%, 450 mg, 11.25 mmol) in anhydrous THF (10 mL) at 0° C. and over 15 minutes. The resulting suspension was stirred for 30 minutes and 2,3-dichloro-5-nitropyridine (1.50 g, 7.77 mmol) was added portionwise. The mixture was stirred at room temperature for 18 hours and then concentrated in vacuo. The resulting crude was partitioned between EtOAc (50 mL) and water (50 mL). The aqueous layer was extracted with EtOAc (2×25 mL). Combined organics were dried over magnesium sulfate and concentrated in vacuo to afford the title compound as an orange oil (2.55 g, 100%).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. concentrationconcentrated in vacuo
  3. customThe resulting crude was partitioned between EtOAc (50 mL) and water (50 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×25 mL)
  5. dry with materialCombined organics were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80224a8033ad44fab1c9f6ae9200e686
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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