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S1+2

S2: S1 (1.00 g, 3.52 mmol, 1.0 eq), Pd(OAc)2 (118 mg, 0.53 mmol, 0.15 eq), Ag2CO3 (970 mg, 3.52 mmol, 1 eq), 3,4-(methylenedioxy) iodobenzene (2.62 g, 10.56 mmol, 3 eq) and pivalic acid (360 mg, 3.52 mmol, 1.0 eq) were placed in a sealed tube and 5.0 mL of tert-butyl alcohol (0.7 M) was added under ambient conditions. The tube was sealed and placed into an 85 °C oil bath for 15 h. The addition of tert-butanol and the supply of heat decompose palladium (II) acetate to reactive palladium (0). The reaction was cooled to room temperature, diluted with dichloromethane (20 mL) and filtered through a pad of celite and concentrated in vacuo to purify the compound and remove any impurities such as silver iodide. The resulting dark red oil was purified by silica gel chromatography (15:15:70 to 20:20:60 dichloromethane:diethyl ether:hexanes) to separate the all cis product from the diastereomer formed. The solvent was chosen to give maximum separation with a majority of hexane due to the small difference in polarity between the two diastereomers. The column separated out a yellow foam which, upon precipitation from toluene (10 mL), gives S2 (775 mg, 54%) as a white solid.





angry 1

My column chromatography DOES NOT work AGAIN!!!!!!!!!!(Oh, hulk punched our "lovely" column. Put your mouse on it to see what happened to the column.)

angry 2