2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → 4-(6-tert-Butyl-cyclohex-1-en-1-yl)-3-methyl-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[C:6]([CH3:19])[CH:5]=1.FC(F)(F)S(O[C:27]1[CH:32]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:31][CH2:30][CH2:29][CH:28]=1)(=O)=O>>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:31]2[CH:32]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:27][CH2:28][CH2:29][CH:30]=2)=[C:6]([CH3:19])[CH:5]=1Participants
3
Procedure
3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Example 28, Step A (1.00 g, 3.62 mmol) and 6-tert-butyl-cyclohex-1-en-1-yl trifluoromethanesulfonate (1.24 g, 4.34 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with a solvent gradient of from 0 to 5% ethyl acetate in hexane, afforded the title compound (0.880 g) as a light yellow oil.