Triethylamine → HCID 67814333, compound

Reaction equation

CCN(CC)CC.[C:8]([O:16][CH2:17][C:18]#[CH:19])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:20](=[N:22]/[OH:23])\[CH3:21]>C(Cl)(Cl)Cl>[C:8]([O:16][CH2:17][C:18]1[O:23][N:22]=[C:20]([CH3:21])[CH:19]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Procedure

To a solution of chloroform, Et3N (0.435 mL, 3.12 mmol), prop-2-ynyl benzoate (1 g, 6.24 mmol), and (E)-acetaldehyde oxime (0.571 mL, 9.37 mmol) at 0° C. was added bleach (23.12 mL, 18.73 mmol). The reaction was stirred overnight before the layers were separated and the aqueous extracted with DCM. The combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (3-methylisoxazol-5-yl)methyl benzoate. LC/MS m/z 218 [M+H]+.