Triethylamine → HCID 54264321, compound

Participants

Reaction Conditions

Reaction Steps

7-Phenylhept-2-enoic acid (7 g; 34 mmol) is dissolved in dry THF and cooled to 0° C. Diphenylphosphinic chloride (ClP(O)Ph2) (7.1 mL; 37 mmol) is added followed by dropwise addition of triethylamine (4.7 mL; 34 mmol). After 45 min at 0° C., a mixture of O-(trimethylsilyl)hydroxylamine (TMSONH2) (4.3 g; 37 mmol) and triethylamine (4.7 mL; 34 mmol) is added dropwise at 0° C. The bath is removed and the reaction is allowed to stir at 20° C. for 2 hours. The reaction is then filtered and the solid is extracted with EtOAc (500 mL). The EtOAc is washed with 60 mL 1 N HCl, 50 mL brine and dried (MgSO4). The resulting solution is concentrated in vacuo to yield a white solid which is purified by tituration with Et2O to obtain 7-phenylhept-2-enoic acid hydroxyamide (3.9 g; 18 mmol). MS (EI) m/e 219 (M+). Anal. (C13H17NO2) C, H, N.

Provenance & Evidence