6,6-Dimethyl-1-cyclohexen-1-yl trifluoromethanesulfonate → 4-(6,6-Dimethyl-cyclohex-1-en-1-yl)-benzoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([Sn](CCCC)(CCCC)CCCC)=[CH:7][CH:6]=1)[CH3:2].FC(F)(F)S(O[C:31]1[C:36]([CH3:38])([CH3:37])[CH2:35][CH2:34][CH2:33][CH:32]=1)(=O)=O>>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:6]=[CH:7][C:8]([C:35]2[C:36]([CH3:38])([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]=2)=[CH:9][CH:10]=1)[CH3:2]Participants
3
Procedure
4-(Tri-n-butyl-stannyl)-benzoic acid ethyl ester of Example 15, Step A (3.20 g, 7.28 mmol) and 6,6-dimethyl-cyclohex-1-en-1-yl trifluoromethanesulfonate (1.71 g, 6.62 mmol) were reacted in the manner of Example 15, Step B. 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 (1.18 g) as a clear oil.
Workup
- customPurification by flash column chromatography on silica gel