Cyclopentadiene → 5-(Pentan-2-ylidene)cyclopenta-1,3-diene

Participants

Reaction Steps

To a solution of 10.00 g (151.3 mmol) of cyclopentadiene in 40 ml of methanol, 18.6 ml (174.2 mmol) of methyl propyl ketone and 4.5 ml (54.7 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (70° C./1 mmHg) to obtain 12.30 g (91.64 mmol) of a yellow liquid (yield: 61%). The analyzed values are given below.

Provenance & Evidence