Propanal → HCID 66730367, compound

Participants

Reaction Steps

A solution of 2,2,4,7,7-pentamethyltricyclo[6.2.1.01.6]undecane-4,5-diol (5b, 1.7 g, 6.6 mmol), propionaldehyde (2.0 g, 33 mmol), lithium bromide (75 mg) and p-toluenesulfonic acid (75 mg) in THF (30 ml) was stirred at r. t. for 1 h, then poured onto saturated aqueous sodium bicarbonate solution (50 ml) and extracted with MTBE (2×50 ml). The combined organic phases were washed with water (2×50 ml), dried (Na2SO4), concentrated in vacuo and the residue (1.9 g) purified by flash chromatography (MTBE/hexane 1:20) and bulb-to-bulb distillation to give 6-ethyl-2,2,4,10,10-pentamethyl-5,7-dioxatetracyclo[9.2.1.01.9,04.8]tetradecane (Ib, 2+98% mixture of isomeric pairs of enantiomers, 0.83 g, 42% yield, colourless oil).

Provenance & Evidence