1-Pentanol → HCID 59700729, compound

HRID 499750Notes

Reaction equation

HRID 499750 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[CH2:4][CH2:5][CH2:6][CH3:7].F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[C:19]([F:22])([F:21])[F:20]>C1COCC1>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([O:8][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:12]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 62761-PentanolHCID 24758Sodium hydrideHCID 949542-Fluoro-5-nitrobenzotrifluoride

Product 1

HCID 59700729HCID 59700729, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (0.7 g, 17.5 mmol) is added to a solution of 1-pentanol (5 ml) in dry THF (25 ml). After stirring at room temperature for 30 min, 3.50 g (16.7 mmole) of 1-fluoro-4-nitro-2-trifluoromethylbenzene is added, and stirring is continued at room temperature overnight. The reaction is quenched with water and extracted with ethylacetate, dried over sodium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluted with 33% dichloromethane/hexane. Removal of solvent provides 4-nitro-1-pentyloxy-2-trifluoromethyl-benzene as pale yellow oil.

Workup

  1. stirringstirring
  2. waitis continued at room temperature overnight
  3. customThe reaction is quenched with water
  4. extractionextracted with ethylacetate
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue is purified by chromatography on silica gel
  8. washeluted with 33% dichloromethane/hexane
  9. customRemoval of solvent

Sources & evidence

ORD record
ord-a5df9d27edad4e118a81d005cdc1a090
Source dataset
uspto-grants-2010_08
Patent number
US07767706B2

Reaction notes

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