Water → HCID 86749779, compound

Participants

Reaction Steps

To a suspension of sodium hydride (3.6 g of a 50% dispersion in oil, 75 mmole) previously washed with petroleum ether 30-50, in 100 ml of tetrahydrofuran (THF), there were added dropwise at 10-20° 13.8 g (75 mmole) of trimethylphosphonoacetate in 100 ml of THF. 15 min after the end of the addition, there was added to the reaction mixture, at 11-15°, a solution of the above-cited indanone (10.2 g, 55 mmole) in THF (150 ml). The mixture was kept under stirring for 16 h at 25°, then it was poured on 500 ml of water and extracted with ether. The combined organic extracts were washed with brine (2 times), dried (Na2SO4) and concentrated until forming an oil which became solid (12.6 g; isomer mixture). This product was crystallized in ether at -30°, to provide 5.56 g of methyl (E)-(5-tert-butyl-1-indanylidene)acetate.

Provenance & Evidence