Hydrochloric Acid → HCID 21088627, compound

HRID 350742Notes

Reaction equation

HRID 350742 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][O:27][C:21]=4[CH:20]=3)[O:11][C:12]=2[CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[CH:4][CH:3]=1.[OH-].[K+].CO.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][O:27][C:21]=4[CH:20]=3)[O:11][C:12]=2[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 23061691HCID 23061691, compound

Product 1

HCID 21088627HCID 21088627, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-[4-(4-chlorophenyl)-2-[3,4-(methylenedioxy)phenyl]-5-oxazolyl]propionate (1.29 g), potassium hydroxide (0.44 g), methanol (20 mL) and tetrahydrofuran (15 mL) was stirred at room temperature for 2 hrs. The reaction mixture was poured into dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated to give 3-[4-(4-chlorophenyl)-2-[3,4-(methylenedioxy)phenyl]-5-oxazolyl]propionic acid (1.22 g, 98%) as a colorless powder. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 199–200° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-95229b941a594acdb01c12f201c22cf2
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

Loading…