Toluene → methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate

Participants

Reaction Steps

To a solution of methyl (S)-4-allyl-8-(benzyloxy)-octanoate (2.37 g, 7.8 mmol) in tetrahydrofuran (70 ml) and water (24 ml) is added a solution of 10 mg/ml of osmium tetroxide in toluene (9.4 ml, 0.37 mmol). Sodium periodate (3.57 g, 16.7 mmol) is added in small portions over a period of 0.5 hour. The mixture is allowed to stir for 1 hour and then poured on water and extracted with ether (3×30 ml). The combined organic extracts are dried, filtered and evaporated to give crude methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate; IR (CH2Cl2): 2727, 1724, 1202, 1100 cm-1.

Provenance & Evidence