ETHYL 5-PHENYL-3-ISOXAZOLECARBOXYLATE

General procedure: N-Hydroxy-1-phenylmethanesulfonamide (0.2 mmol), n-Bu4NIO4 (0.2 mmol), I2 (0.1 mmol) and AIBN (10percent) were added to a 25 mL roundbottom flask. A solution of the alkene (excess) or alkyne (0.2 mmol) in anhydrous CH2Cl2 (2 mL) was injected via a syringe and the mixture was stirred under visible-light irradiation for 10 h at r.t. The mixture was diluted with CH2Cl2 (10 mL) and washed with saturated aqueous NaCl (2 10 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification was accomplished by column chromatography on silica gel H with petroleum ether/ethyl acetate (20:1) as the eluent to give the pure product.INTERMEDIATE 54 - PREPARATION OF ethyl S-phenylisoxazole-δ-carboxylate. ; A mixture of ethyl propriolate (0.657 mlGeneral procedure: To a solution of the appropriate aldoxime (1.2 mmol, 1.0 equiv) in ethyl methyl ketone (10 mL) was added appropriately substituted alkyne (1.32 mmol, 1.1 equiv) followed by alkyl nitrite 4 (1.32 mmol, 1.1 equiv). After 5 min stirring at r.t., the turbid reaction mixture became a clear solution and the reaction mixture was stirred at 65 °C until the aldoxime had been consumed. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (EtOAc–n-hexane, 1:9 v/v) to afford the desired compound.

Molecular Weight:217.22
XLogP3:2.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:217.07389321
Monoisotopic Mass:217.07389321
Topological Polar Surface Area:52.3
Heavy Atom Count:16
Complexity:238
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes