Sodium Bicarbonate → HCID 69834378, compound

Participants

Reaction Steps

Anhydrous copper sulfate (478 mg, 3.0 mmol, 1.5 equiv), p-toluenesulfonic acid monohydrate (76 mg, 0.4 mmol, 0.2 equiv), and pyridine (24 μl, 0.3 mmol, 0.15 equiv) are added to a solution of (S)-(E)-4,4-dimethyl-5-ethyl-heptane-1,3-diol 28 (372 mg, 2.0 mmol) in acetone (30 ml). The mixture is stirred for 24 h at r.t. Saturated aqueous sodium bicarbonate solution (40 ml) is added, and the aqueous layer is extracted with diethyl ether (4×60 ml). The combined organic extracts are dred over magnesium sulfate and carefully concentrated in vacuo. Purification of the residue by flash column chromatography (pentane/diethyl ether 40:1) affords the title compound 29 (812 mg, 90%) as a colourless oil. 13C-NMR (50 MHz, CDCl3): δ=146.2; 119.3; 98.3; 74.2; 60.4; 42.9; 29.9; 26.2; 24.3; 21.2; 19.2; 14.4; 13.7

Provenance & Evidence