Benzyl Alcohol → Benzyl cyclopent-3-en-1-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of cyclopent-3-ene-1-carboxylic acid (2.0 g, 17.8 mmol) and DPPA (6.05 g, 22.0 mmol) in toluene (50 mL) was added TEA (2.0 g, 22.0 mmol) dropwise at 0° C. The resulting mixture was then warmed and heated at 90° C. for 1 hour. After being added phenylmethanol (4.0 g, 40 mmol), the mixture was heated at 90° C. for additional 4 hours and then concentrated in vacuo. The residue was purified by silica-gel chromatography to afford benzyl cyclopent-3-en-1-ylcarbamate as a white solid (1.9 g).

Provenance & Evidence