Ethyl (E)-3-(2-Methoxyphenyl)-2-butenoate.docVIP

Ethyl (E)-3-(2-Methoxyphenyl)-2-butenoate /molbank/m0071.htm Molecules 1998, 3, M71 Ethyl (E)3(2Methoxyphenyl)2butenoate Martin J. Stoermer* and John T. Pinhey Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia. * Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia. Phone: +61 3 990 39000, Fax: +61 3 e-mail: martin.stoermer@.au, .au/martin/ Received: 27 February 1998 / Published: 6 March 1998 The general part of the experimental section [1] has been presented elsewhere. To the solution of lithium diisopropylamide prepared from diiisopropylamine (6.5 ml, 46 mmol) and n-butyllithium (2.2 M, 20 ml, 44 mmol) in dry tetrahydrofuran (50 ml) at 0° was added triethylphosphonoacetate (8.74 ml, 44 mmol) at 0°. The mixture was stirred at room temperature for 10 minutes and o-methoxyacetophenone (6.1 ml, 44 mmol) was added dropwise. The mixture was refluxed for 6 hours and stirred at room temperature overnight. The mixture was poured onto hydrochloric acid (3M, 80 ml) and extracted into ether (100 ml). The ether extract was washed with hydrochloric acid (3M, 2x100 ml), water (2x100 ml), brine (50 ml), dried (Na2SO4), filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography (ethyl acetate/light petroleum 1:9), followed by radial chromatography (ethyl acetate/light petroleum 2:98) to yield ethyl (E)-3-(2-methoxyphenyl)-2-butenoate(3.78 g, 39%) as a colourless oil. B.p. 159°/12 mmHg (Kugelrohr) (lit.[2] (E) and (Z)-mixture, 162-4°/16 mmHg Anal. calc. for C13H16O3 (220.26): C 70.9, H 7.3; found: C 71.3, H 7.7. UV (ethanol) 292sh (4479), 262 (7870), 218 (18116) nm. IR (film) 2977, 1695 (s, C=O), 1634, 1489, 1260, 1237, 1176(s), 1046, 740 cm-1. 1H-NMR (400 MHz, CDCl3) 1.29 (3H, t, J 7.2 Hz, -OCH2CH3), 2.49 (3H, d, J 1.5 Hz, CH3), 3.81 (3H, s, OCH3), 4.20 (2H, q, J 7.2 Hz, -OCH2CH3),