Formaldehyde → HCID 57891811, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 3-cyclopentene-1-carboxylate (8.4 g, 50.0 mmole) [JACS, 1983, 105, 2435-2439] in toluene (150 mL) and EtOH (75 mL) was added paraformaldehyde (11.0 g, 250 mmole), N-hydroxybenzylamine hydrochloride (11.8 g, 75 mmole) and triethylamine (10.4 mL, 75 mmole). After 24 hours at 80° C., the reaction solution was concentrated under vacuum and redissolved in hexanes/EtOAc, 4:1 (200 mL) and filtered. The organic solution was concentrated and then purified on silica (hexanes/EtOAc, 4:1) to give the title compound (13.0 g, 86%) as a light yellow oil: LC-MS (ES) m/e 304 (M+H)+.

Provenance & Evidence