Methyl iodide → HCID 68854301, compound

Participants

Reaction Steps

A solution of 3b (1.0 g, 3.8×10−3 mol) in DMF (5 ml) was added to a THF (8 ml) suspension of sodium hydride (0.27 g of 50% dispersion in mineral oil, washed twice with hexane, 5.6×10−3 mol). After 3 h stirring at r. t., methyl iodide (1.6 g, 0.011 mol) was added under cooling and the reaction mixture was stirred at r. t. for additional 4 h, poured into ice-cold 2M HCl (100 ml) and extracted with MTBE (2×100 ml). The organic phase was washed with brine (2×50 ml), dried (MgSO4), concentrated in vacuo and purified by flash chromatography (MTBE/hexane 1:20) to give 5-(1-methoxyprop-2-yl)-2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undec-5-ene (8b, 0.73 g, 69% yield, colourless oil).

Provenance & Evidence