Sodium Thiosulfate → HCID 57554761, compound

Participants

Reaction Steps

Tert-butyldimethyl(1-(4-octylphenyl)but-3-enyloxy)silane (19.108 g, 51.0 mmol) and NMO (7.17 g, 61.2 mmol) were combined in acetone (227 ml) and water (28.3 ml). Osmium tetroxide (32.0 ml, 2.55 mmol) was added and the reaction stirred for about 2 h. TLC in 1:1 EtOAc/heptane showed reaction complete. Sodium thiosulfate (8.06 g, 51.0 mmol) was added and the reaction stirred for about 3 h resulting in a coarse black precipitate. The solution was poured over 150 mL of silica gel and washed product through thoroughly or washed product through?with ethyl acetate until no more product was eluting as shown by TLC (˜700 mL EtOAc). The resulting 4-(Tert-butyldimethylsilyloxy)-4-(4-octylphenyl)butane-1,2-diol (14.68 g, 35.9 mmol) and molecular sieves (5 g) (Aldrich) were combined in THF (359 ml) under nitrogen. TBAF (35.9 ml, 35.9 mmol) (Aldrich) was added and the reaction stirred for about 16 h. The mixture was filtered and the solvents evaporated to provide an orange/brown oil. The oil was passed through a pad of silica gel (150 mL) and washed through with ethyl acetate. Product eluted slowly and took almost 2 L of EtOAc for all product to elute. The solvents were removed under reduced pressure to provide 4-(4-octylphenyl)butane-1,2,4-triol (12.045 g, 40.9 mmol, 114% yield) as an orange oil: LC/MS (Purity QC) Rt=3.84, 3.89 min.; MS m/z: 294.40, 294.02 (M+H)+.

Provenance & Evidence