6-iodohex-1-ene

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 60 mL DMF suspension of potassium carbonate (3.98 g, 28.8 mmol) were added hydroquinone (1.05 g, 9.54 mmol) and 6-iodo-1-hexene (6.01 g, 28.6 mmol) at room temperature. The reaction mixture was warmed to 100° C. and stirred for 10 h. After cooling to room temperature, the mixture was quenched with 10% aqueous sodium hydroxide (60 mL). The mixture was extracted with diethyl ether (3×50 mL). The combined organic solutions were washed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The crude product was purified by MPLC (80:1, hexane:ethyl acetate) to give the olefin 10 (1.86 g, 71%) as a white solid (mp=29.0°-30.0° C.); Anal. Calcd for C18H26O2 : C, 78.79%; H, 9.55%. Found: C, 78.69%; H, 9.37%; cap gc: tR =10.49 min; column: 25 m×0.25 mm, OV-101; temp prog: 50° C. /4 min/20° C. min-1 / 250° C./ 0 min; tlc: Rf =0.48 in 9:1 hexane:ethyl acetate. After cooling to room temperature the mixture was quenched with 10% aqueous sodium hydroxide (60 mL) The mixture was extracted with diethyl ether (3×50 mL) The combined organic solutions were washed with aqueous saturated sodium chloride dried over anhydrous magnesium sulfate concentrated The crude product was purified by MPLC (80:1, hexane:ethyl acetate)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 60 mL DMF suspension of potassium carbonate (3.98 g, 28.8 mmol) were added hydroquinone (1.05 g, 9.54 mmol) and 6-iodo-1-hexene (6.01 g, 28.6 mmol) at room temperature. The reaction mixture was warmed to 100° C. and stirred for 10 h. After cooling to room temperature, the mixture was quenched with 10% aqueous sodium hydroxide (60 mL). The mixture was extracted with diethyl ether (3×50 mL). The combined organic solutions were washed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The crude product was purified by MPLC (80:1, hexane:ethyl acetate) to give the olefin 10 (1.86 g, 71%) as a white solid (mp=29.0°-30.0° C.); Anal. Calcd for C18H26O2 : C, 78.79%; H, 9.55%. Found: C, 78.69%; H, 9.37%; cap gc: tR =10.49 min; column: 25 m×0.25 mm, OV-101;temp prog: 50° C./4 min/20° C. min-1 /250° C./0 min; tlc: Rf =0.48 in 9:1 hexane:ethyl acetate. After cooling to room temperature the mixture was quenched with 10% aqueous sodium hydroxide (60 mL) The mixture was extracted with diethyl ether (3×50 mL) The combined organic solutions were washed with aqueous saturated sodium chloride dried over anhydrous magnesium sulfate concentrated The crude product was purified by MPLC (80:1, hexane:ethyl acetate)