Sodium ethoxide → 4-(4-Chlorophenyl)-2-ethoxy-5-oxazolepropionic acid

HRID 2300674Notes

Reaction equation

HRID 2300674 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[O-:19][CH2:20][CH3:21].[Na+].[Na]>C(O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([O:19][CH2:20][CH3:21])[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 118082582-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid

Product 1

HCID 544728364-(4-Chlorophenyl)-2-ethoxy-5-oxazolepropionic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid (1.43 g) was added to an ethanol solution of sodium ethoxide prepared from sodium (0.35 g) and ethanol (15 ml), and stirred under reflux for 30 minutes. The solvent was evaporated, and water was added to the residue, which was then acidified with 2 N hydrochloric acid. The crystals thus precipitated were collected by filtration to obtain 4-(4-chlorophenyl)-2-ethoxy-5-oxazolepropionic acid (1.40 g, 95%). This was recrystallized from ethanol to give colorless prisms. mp 148-149° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. customThe solvent was evaporated
  3. additionwater was added to the residue, which
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-28ae0a196bae49f3a39144645325b85f
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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