Triphenylphosphine → HCID 86611582, compound

Participants

Reaction Steps

A solution of 5.4 g (15.9 mmol) of [(R)-3,7-dimethyl-1-(5-oxo-tetrahydro-furan-2-yl)oct-6-enyl]-carbamic acid tert-butyl ester (preparation of aldehyde in step g of example 6) in a mixture 200 ml DCM and 10 ml MeOH is cooled to −70° C. After addition of 0.63 g (7.5 mmol) NaHCO3 a stream of O3 in O2 is passed through the stirred mixture till a blue color persists. The excess ozone is removed by passing through more oxygen. After addition of 5.0 g (19 mmol) triphenylphosphine the mixture is allowed to warm up at rt and stirred for 4 h. The mixture is filtered and concentrated in vacuo. Chromatography on silica gel (EtOAc/Hexane 1:1) gives the title aldehyde.

Provenance & Evidence