[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16](B(O)O)=[CH:17][C:18]2[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=2[CH:24]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.I/[C:45](/[CH3:51])=[CH:46]\[C:47]([O:49][CH3:50])=[O:48]>O.C(COC)OC>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16](/[C:45](/[CH3:51])=[CH:46]\[C:47]([O:49][CH3:50])=[O:48])=[CH:17][C:18]2[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=2[CH:24]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]A mixture of tetrakis(triphenyl-phosphine)palladium (155 mg), 3-[5-(tert-butyldimethylsilyloxy)pentyloxy]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaleneboronic acid (300 mg, 0.67 mmol), a 2M solution of potassium carbonate in water (0.67 ml) and methyl (Z)-3-iodo-2-butenoate (Ma, S. & Lu, X.; J. Chem. Soc. Chem. Com., pp. 1643-1644 (1990)) (182 mg) in dimethoxyethane (DME) (10 ml) was heated to reflux for 24 h. The solution was poured into a mixture of water and ethyl acetate. The organic phase was washed twice with water, dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C. The desired compound was purified by flash chromatography on a silica column.
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