Iodoethane → HCID 68698574, compound

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](I)[CH3:21]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[O:9][CH2:10][CH2:11][O:12]2)[CH:5]=[C:4]([O:13][CH2:20][CH3:21])[CH:3]=1

Participants

Procedure

To a solution of 3-bromo-5-[1,3]dioxolan-2-yl-phenol (0.53 g, 2.16 mmol, 1.0 equiv) in DMF (2 mL) was added K2CO3 (0.33 g, 2.38 mmol, 1.1 equiv) and ethyl iodide (0.19 mL, 0.37 g, 2.38 mmol, 1.1 equiv) and the reaction mixture stirred under Ar at rt for 18 h. The K2CO3 was removed by filtration, the filtrate extracted with cyclohexane (3×50 mL), the combined organic phases washed with water (2×50 ml) and dried over MgSO4. The solvent was removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (6:1) providing 0.42 g (72%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.40 (t, J=7.0 Hz, 3H), 4.01-4.10 (m, 6H), 5.75 (s, 1H), 6.93-6.94 (m, 1H), 7.02-7.04 (m, 1H), 7.19-7.20 (m, 1H). MS (EI): 273.0 [M]+.