反应详情

温度

0 °C

Diisopropyl azodicarboxylate (2.63g, 0.013 mol) was added dropwise over a 5 min period to a cold (0° C.) mixture of triphenylphosphine (3.40g, 0.013 mol) in tetrahydrofuran (20 mL). The mixture was stirred at 0° C. for 0.5h. A solution of thioacetic acid (0.99g, 0.013 mol) and 2-ethylidene-6-methyl5-hepten-1-ol (1.00g, 0.0065 mol) in tetrahydrofuran (20 mL) was then added dropwise over a 0.5h period to the cold (0° C.) reaction mixture. The mixture was stirred for 1h at 0° C. and then 1h at 25° C. The solvent was removed under reduced pressure. Hexane (40 mL) was added and the mixture was filtered to remove solids. Work-up, chromatography, and kugelrohr distillation (bath temp. 100° C., 0.5 mm) provided 1.15g of 2-ethylidene-6-methyl-5-hepten-1-thiol acetate (GLC purity 94.7%; isomers not separated). NMR (60 MHz, CDCl3) δ 1.62 and 1.68 (6H, 2s), 1.63 (3H, d, J=6 Hz) 2.1 (4H, broad s), 3.57 (2H, broad s), 5.0-5.3 (1H, m), 5.49 (1H, q, J=6Hz); IR (film) vmax 2920, 1685, 1430, 1125 940 cm-1 ; MS m/e 212, 197, 169, 136, 69, 43.

1. customat 25° C
2. customThe solvent was removed under reduced pressure
3. additionHexane (40 mL) was added
4. filtrationthe mixture was filtered
5. customto remove solids
6. distillationWork-up, chromatography, and kugelrohr distillation (bath temp. 100° C., 0.5 mm)