4-Fluorobenzamide → Ethyl[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetate

HRID 227449

Reaction equation

HRID 227449 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH:12]([CH3:21])[C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[O:7][C:12]=1[CH3:21])[CH3:19]

Participants

4

Reactant 2

HCID 715724-FluorobenzamideHCID 12780443Ethyl 4-bromo-3-oxopentanoate

Product 1

HCID 85817159Ethyl[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetateYield 48.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 4fluorobenzamide (12.9 g) and ethyl 4bromo-3-oxopentanoate (Chem Abs No. 3618769-6; 5.24 g) in anhydrous toluene (120 ml) was heated at 140° C. for 19 h, using a Dean-Stark trap. The solution was allowed to cool, filtered, and the residual solid washed with toluene (30 ml). The combined filtrate and washings were concentrated in vacuo to give a brown oil, which was purified by Biotage flash chromatography on silica gel (90 g column), eluting with ethyl acetate:cyclohexane (5:95, 7.5:92.5, 10:90), to give the title compound as a yellow solid (2.98 g).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. washthe residual solid washed with toluene (30 ml)
  4. concentrationThe combined filtrate and washings were concentrated in vacuo
  5. customto give a brown oil, which
  6. customwas purified by Biotage flash chromatography on silica gel (90 g column)
  7. washeluting with ethyl acetate:cyclohexane (5:95, 7.5:92.5, 10:90)

Sources & evidence

ORD record
ord-4a4170c5aeee4106806b662e8d978de3
Source dataset
uspto-grants-2009_07
Patent number
US07560548B2

Linked notes

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