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

HRID 2211968Notes

Reaction equation

HRID 2211968 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>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][C:12]([CH3:21])=[C:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=2)=[CH:4][CH:3]=1

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]acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-fluorobenzamide (12.9 g) and ethyl 4-bromo-3-oxopentanoate (Chem Abs No. 36187-69-6; 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 thetitle 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-8605836bbf284d16bcbb7e53c88b075e
Source dataset
uspto-grants-2006_09
Patent number
US07101882B2

Reaction notes

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