Tetrapropylammonium → (S)-9-hydroxy-5,9-dimethyl-decanal

Participants

Reaction Steps

5.68 g of 4-methylmorpholine N-oxide (monohydrate) (NMO) and 31.5 g of molecular sieves (powder, 4A) in 200 ml of abs. CH2Cl2 were stirred for 0.25 h at ambient temperature. 500 mg of tetrapropylammonium perrhutenate (TPAP) was added, before a solution of 4.59 g of (R)-5,9-dimethyl-decane-1,9-diol in 20 ml of abs. CH2Cl2 was added within 1 h. 15 minutes later, the reaction mixture was filtered and the solvents removed i.V. Flash chromatography (SiO2, hexane/AcOEt=7/3) afforded 3.103 g of (S)-9-hydroxy-5,9-dimethyl-decanal as colorless oil, 98.7% pure according to GC.

Provenance & Evidence