Triethylamine → 7-Methanesulfonyl-1-heptene

Participants

Reaction Conditions

Reaction Steps

This example illustrates the synthesis of 1-(6-Heptenyl)-3,7-dimethylxanthine (CT1534). To a solution of 6-hepten-1-ol (6.00 g, 52.6 mmol) in dichloromethane (120 ml) at 0° C. was added methanesulfonyl chloride (6.07 g, 4.0 ml, 53.0 mmol) followed by triethylamine (7.79 g, 77.0 mmol). After stirring for 10 min at 0° C., the reaction was allowed to warm to 25° C. and stirred for 2 hr. The reaction was poured into water (100 ml) and extracted with dichloromethane (2×100 ml). The organic portions were combined, dried (magnesium sulfate), and evaporated to give the 7-methanesulfonyl-1-heptene as a yellow oil (9.30 g, 93%), which was used without further purification.

Provenance & Evidence