Water → 2-[(1,1,1,3,3,3-Hexafluoropropan-2-yl)oxy]-5-nitropyridine

HRID 564291Notes

Reaction equation

[H-].[Na+].[F:3][C:4]([F:12])([F:11])[CH:5]([OH:10])[C:6]([F:9])([F:8])[F:7].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.O>C1COCC1>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([O:10][CH:5]([C:6]([F:9])([F:8])[F:7])[C:4]([F:12])([F:11])[F:3])=[N:15][CH:16]=1)([O-:22])=[O:21]

Participants

Conditions

Temperature: 5 °C

Procedure

2.45 g (61.2 mmol) of sodium hydride was introduced to 15 ml of THF and cooled to 5° C., and then 10.6 g of 1,1,1,3,3,3-hexafluoro-2-propanol was added dropwise thereto. The resulting solution was stirred at 5° C. for 30 minutes, and then 5.0 g of 2-chloro-5-nitropyridine dissolved in 10 ml of THF was added dropwise thereto and stirred at room temperature for 3 hours. The reaction solution was allowed to stand at room temperature for 3 days, the water was added thereto, and the mixture was extracted with ethyl acetate and then washed with saturated salt water. The resultant was dried over anhydrous magnesium sulfate, and then the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane AcOEt=10:1) to obtain 8.4 g of the desired product (Yield: 92%) as yellow oil.

Workup

additionwas added dropwise
stirringstirred at room temperature for 3 hours
waitto stand at room temperature for 3 days
extractionthe mixture was extracted with ethyl acetate
washwashed with saturated salt water
dry with materialThe resultant was dried over anhydrous magnesium sulfate
customthe solvent was removed under a reduced pressure
customto obtain a residue
customThe resulting residue was purified by silica gel column chromatography (n-hexane AcOEt=10:1)

Sources & evidence

ORD record: ord-edd9f7910af345bb91720f1d03830d97
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067638B2

Reaction notes

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