6,6-Dimethyl-1-cyclohexen-1-yl trifluoromethanesulfonate → 4-(6,6-Dimethyl-cyclohex-1-en-1-yl)-3-methyl-benzoic acid methyl ester

HRID 1794003Notes

Reaction equation

HRID 1794003 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[C:32]([CH3:34])([CH3:33])[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[C:32]([CH3:34])([CH3:33])[CH2:27][CH2:28][CH2:29][CH:30]=2)=[C:6]([CH3:19])[CH:5]=1

Participants

3

Reactant 2

HCID 106349276,6-Dimethyl-1-cyclohexen-1-yl trifluoromethanesulfonateHCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester

Product 1

HCID 696526034-(6,6-Dimethyl-cyclohex-1-en-1-yl)-3-methyl-benzoic acid methyl esterYield 55.8%

Procedure

3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Example 28, Step A (0.300 g, 1.09 mmol) and 6,6-dimethyl-cyclohex-1-en-1-yl trifluoromethanesulfonate (0.338 g, 1.31 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with 5% ethyl acetate in hexane, afforded the title compound (0.157 g) as a clear oil.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bc56aad4fb4548569889da115299d63d
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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