Nitrogen → HCID 86649086, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask equipped with a magnetic stirring bar and a reflux condenser was added 3-thiophen-2-yl-oxirane-2-carboxylic acid ethyl ester (2.2 g, 11 mmol), and NaN3 (2.15 g, 33 mmol) in 25 ml of MeOH. NH4Cl (1.77 g, 33 mmol) was then added and the reaction mixture was heated to 65° C. and stirred for 4 hours. The reaction mixture was then concentrated under reduced pressure and the residue was dissolved in EtOAc and washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was then dissolved in 35 ml acetonitrile and heated to 50° C. in a round bottom equipped with a condenser. PPh3 (3.18 g, 12.1 mmol) was added slowly (N2 evolved) and then the flask was fitted with a condenser and heated to 83° C. for 2 hours. The resulting mixture was filtered and the filtrate concentrated under reduced pressure. To the residue was added 5% EtOAc in pentane and the precipitate was filtered off. The filtrate was then subjected to silica gel column chromatography using 10% EtOAC in hexanes to afford the title compound as a purple oil in 62% yield over two steps. The NMR spectra were in accordance with literature (Solladie-Cavallo, A.; Lupattelli, P.; Bonini, C; De Bonis, M. Tetrahedron Lett. 2003, 44, 5075). 1H NMR (CDCl3, 300 MHz) δ: 7.22 (d, J=5.0 Hz, 1H), 7.09 (d, J=3.4 Hz, 1H), 6.99 (dd, J=5.0 Hz, 3.4 Hz, 1H), 4.30 (qd, J=7.0 Hz, 1.6 Hz, 2H), 3.54 (d, J=7.0 Hz, 1H), 2.73 (d, J=6.2 Hz, 1H), 2.2-1.9 (bt, 1H), 1.37 (t, J=7.0 Hz, 3H) ppm. 13C NMR (CDCl3, 50 MHz) δ: 171.3, 142.6, 127.1, 125.3, 124.5, 61.7, 40.4, 37.0, 14.23 ppm. (ESI MS) [MH]+=198.1

Provenance & Evidence