Water → HCID 12774760, compound

Participants

Reaction Conditions

Reaction Steps

70 ml of Jones solution containing 19.32 g (0.193 mole) of CrO3 are added dropwise at -20° to -25° C. to a solution of 49.3 g (0.136 mole) of the alcohol of Example 2 in 350 ml of acetone. (Jones solution comprises 26.7 g of CrO3, 23 ml of concentrated H2SO4, and 21 ml of H2O made up to 100 ml.) The solution is stirred for a further 2 hours at -20° C., and an excess of i-propanol is then added at this temperature. The solution is neutralized with triethylamine, allowed to warm up to room temperature and filtered over Celite. The residue is washed thoroughly with acetone, the filtrate is concentrated almost to dryness and ethyl acetate is added to the residue. The organic phase is washed several times with half-saturated NaCl solution, and the combined aqueous phases are saturated with NaCl and extracted several times with ethyl acetate. The combined extracts are dried over MgSO4, concentrated and filtered over a short column (5 times the quantity of silica gel, developing solvent: ethyl acetate).

Provenance & Evidence