Hydrochloric Acid → HCID 69560894, compound

To a solution of diethyl malonate (10.3 g) in tetrahydrofuran (80 ml) was gradually added sodium hydride (60%, oil, 2.34 g) at 0° C. The mixture was stirred for 10 min and a solution of 4-chloromethyl-5-(4-methylthiophenyl)isoxazole (7.00 g) in tetrahydrofuran (70 ml) was added dropwise at 0° C. The mixture was stirred at room temperature for 8 hr. The reaction mixture was poured into water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was dissolved in a mixture of 6N hydrochloric acid (50 ml) and acetic acid (100 ml), and heated under reflux for 5 hr. The reaction mixture was concentrated, and water was added to the residue to give colorless crystals (4.68 g, yield 61%) of 3-[5-(4-methylthiophenyl)-4-isoxazolyl]propionic acid. The crystals were recrystallized from ethyl acetate-isopropyl ether to give a colorless prism. melting point: 124–125° C.

1. customat 0° C
2. stirringThe mixture was stirred at room temperature for 8 hr
3. extractionextracted with ethyl acetate
4. washThe ethyl acetate layer was washed with saturated brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in a mixture of 6N hydrochloric acid (50 ml) and acetic acid (100 ml)
8. temperatureheated
9. temperatureunder reflux for 5 hr
10. concentrationThe reaction mixture was concentrated
11. additionwater was added to the residue

ORD record

ord-629b8ac031ea49f999f8cb9c88ff90fa

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07022725B2