Formaldehyde → 4-(S)-methyl-8-methylnon-7-enyl alcohol

Participants

Reaction Steps

This example illustrates the synthesis of 1-(4-(S)-Methyl-8-methylnon-7-enyl)-3,7-dimethylxanthine (CT2536S). To a suspension of magnesium (2.74 g, 140 mmol) and a crystal of iodine in tetrahydrofuran (15 ml) was added (S)-citronellyl bromide (5.0 g, 22.8 mmol) in tetrahydrofuran (10 ml) over 30 min and the reaction stirred for a further 30 min after the addition was complete. The solution was added via a canula over 5 min to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (15 ml) and stirred at 25° C. for 6 hr. Saturated ammonium chloride (40 ml) was added and extracted with diethyl ether (2×30 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give 4-(S)-methyl-8-methylnon-7-enyl alcohol as a clear liquid (3.25 g, 84%).

Provenance & Evidence