Water → 2,5-Dimethyl-4-[2-(4-nitrophenoxy)ethyl]-1,3-oxazole

HRID 4402

Reaction equation

HRID 4402 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[C:5]([CH2:7][CH2:8][OH:9])[N:6]=1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.[H-].[Na+].O>CN(C)C=O>[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[C:5]([CH2:7][CH2:8][O:9][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 201524282-(2,5-Dimethyl-4-oxazolyl)ethanol

Product 1

HCID 137139512,5-Dimethyl-4-[2-(4-nitrophenoxy)ethyl]-1,3-oxazoleYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2,5-Dimethyl-4-oxazolyl)ethanol (17.0 g) and 4-fluoronitrobenzene (17.0 g) were dissolved in N,N-dimethylformamide (150 ml), and 60% sodium hydride in oil (6.0 g) was added dropwise to the solution under vigorous stirring. After stirring at room temperature for 1 hour, the reaction mixture was poured into water (1 l) and the crystals which separated out were collected by filtration and recrystallized from ethyl acetate-hexane to give 4-[2-(2,5-dimethyl-4-oxazolyl)ethoxy]nitrobenzene (27.5 g. 87.0%). Colorless columns, m.p. 97°-98° C. Elemental analysis for C13H14N2O4, Calcd.: C, 59.94; H, 5.38; N, 10.68. Found: C, 59.72; H, 5.44; N, 10.63.

Workup

  1. customthe crystals which separated out
  2. filtrationwere collected by filtration
  3. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2feeb981fa26423a88ce70051e08a909
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

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