Nitroethane → 5-(4-Fluorophenyl)-3-methyl-1,2-oxazole

HRID 1669805Notes

Reaction equation

HRID 1669805 reaction equation
C1(N=C=O)C=CC=CC=1.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)#[CH:11].[N+:19]([CH2:22][CH3:23])([O-])=[O:20].C(N(CC)CC)C>C1C=CC=CC=1.O>[CH3:23][C:22]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[O:20][N:19]=1

Participants

7

Reactant 4

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 5226271-Ethynyl-4-fluorobenzene

Product 1

HCID 125395405-(4-Fluorophenyl)-3-methyl-1,2-oxazole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

2.41 ml (22.19 mmol) of phenyl isocyanate are added dropwise at room temperature to a solution of 2 g (16.64 mmol) of 1-ethynyl-4-fluorobenzene, 0.4 ml (5.55 mmol) of nitroethane and 0.15 ml (1.11 mmol) of triethylamine in 40 ml of benzene. The reaction mixture is then stirred under reflux for 12 h. After cooling, the suspension is mixed with water (20 ml) and stirred at room temperature for a further 4 h. The precipitate is filtered off with suction and washed with benzene (10 ml). The organic phase of the filtrate is separated off, dried with magnesium sulfate and concentrated. The residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). 0.62 g (63% of theory) of the title compound is obtained as a colorless oil.

Workup

  1. temperatureunder reflux for 12 h
  2. temperatureAfter cooling
  3. stirringstirred at room temperature for a further 4 h
  4. filtrationThe precipitate is filtered off with suction
  5. washwashed with benzene (10 ml)
  6. customThe organic phase of the filtrate is separated off
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-49495c128ba34c28aa01ed01b4c80247
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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