Diethyl Malonate → HCID 13688474, compound

Participants

Reaction Steps

A solution of sodium (0.408 g, 17.7 mmol) in ethanol (50 ml) under nitrogen was treated with diethyl malonate, (2.84 g, 17.7 mmol) followed by 1-bromo-2-(4-[(Z)1-undecenyl]phenoxy)ethane, (1.30 g, 3.68 mmol). The solution was refluxed 30 h, then cooled and evaporated in vacuo to dryness. The residue was partitioned between ethyl acetate and water and the organic phase separated, washed with water, and dried, (MgSO4). Evaporation in vacuo gave 2.0 g of a yellow oil which was purified by column chromatography using silica gel, eluting with dichloromethane: n-hexane, [2:3] to yield 510 mg (32%) of the title compound as a colourless oil. νmax (film) 1510, 1570 (weak) 1608, 1735, 1753 cm-1 δ(CDCl3) 0.84 (3H, distorted t, terminal CH3), 1.25 (3H, t, J 7 Hz ester CH3), 1.25 (14H, m, (CH2 )7), 2.31 (4H, m, OCH2CH2, allylic CH2), 3.63 (1H, t, J 7 Hz, CH(CO2Et)2), 4.01 (2H, t, J 7 Hz, OCH2), 4.18 (4H, q, J 7 Hz, ester CH2), 5.54 (1H, d.t, Jd 12 Hz, Jt 7 Hz, =CH--alkyl), 6.31 (1H, d, J 12 Hz, ArCH=), 7.02 (4H, ABq, Δν 34 Hz, J 9 Hz, C6H4).

Provenance & Evidence