HCID 13646804, compound → 3-[4-(4-Chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propanoic acid

HRID 1982442Notes

Reaction equation

HRID 1982442 reaction equation
Cl[CH:2]([CH2:6][C:7]1[O:11][C:10]([CH3:12])=[N:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:3]([OH:5])=[O:4]>C(O)(=O)C.[Zn]>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:8]2[N:9]=[C:10]([CH3:12])[O:11][C:7]=2[CH2:6][CH2:2][C:3]([OH:5])=[O:4])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 13646804HCID 13646804, compound

Product 1

HCID 132932823-[4-(4-Chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propanoic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (0.87 g) was added portionwise under stirring at 80°-90° C. into a suspension of 2-chloro-3-[4-(4-chlorophenyl)-2-methyl-5-oxazolyl]-propionic acid (1.0 g) in acetic acid (10 ml). After heating for 40 minutes, undissolved materials were filtered off and water was added to the filtrate. The resulting crystalline precipitate was collected by filtration to give 4-(4-chlorophenyl)-2-methyloxazole-5-propionic acid, yield 0.83 g (94.3%). Recrystallization from ethanol gave colorless needles, m.p. 211°-212° C. The IR and NMR spectra of this compound were in agreement with those of the compound obtained in Example 5.

Workup

  1. temperatureAfter heating for 40 minutes
  2. filtrationundissolved materials were filtered off
  3. additionwater was added to the filtrate
  4. filtrationThe resulting crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-02225793a70845be9512643b3a9a5b9d
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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