[CH2:1](O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1C(C)=CC(C)=CC=1C.[Cl-].[Li+].CS([Cl:26])(=O)=O>CN(C=O)C.CCOCC>[CH2:1]([Cl:26])/[CH:2]=[CH:3]\[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1A solution of the cinnamyl alcohol (1-1) (17.8 g, 133 mmol; Fukuda, et al., Tetrahedron 55, 1999, pp 649-664) in DMF (75 mL) was treated with collidine (35.1 mL, 32.2 g, 266 mmol), lithium chloride (11.2 g, 266 mmol), and methanesulfonyl chloride (20.7 mL, 30.6 g, 173 mmol) at room temperature. After stirring for 12 h, the reaction was diluted with Et2O (300 mL) and washed with water, satd aq NH4Cl, and brine. The organic solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (SiO2, 5% EtOAc/hexanes) to give allyl chloride (1-2) as a colorless oil. 1NMR (500 MHz, CDCl3) δ 7.40 (m, 2H), 7.32 (m, 3H), 6.68 (d, J=11 hz, 1H), 5.94 (m, 1H), 4.30 (m, 2H) ppm.
Loading…
