2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → 3-Methyl-4-(3,3,5,5-tetramethyl-cyclohex-1-en-1-yl)-benzoic acid methyl ester

HRID 1794015Notes

Reaction equation

HRID 1794015 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[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29]([CH3:36])([CH3:35])[CH:28]=1)(=O)=O>>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:27]2[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29]([CH3:36])([CH3:35])[CH:28]=2)=[C:6]([CH3:19])[CH:5]=1

Participants

3

Reactant 2

HCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 110873803,3,5,5-Tetramethylcyclohex-1-en-1-yl triflate

Product 1

HCID 696525633-Methyl-4-(3,3,5,5-tetramethyl-cyclohex-1-en-1-yl)-benzoic acid methyl esterYield 75.2%

Procedure

3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Example 28, Step A (0.500 g, 1.81 mmol) and 3,3,5,5-tetramethyl-cyclohex-1-en-1-yl trifluoromethanesulfonate (0.621 g, 2.17 mmol) were reacted by the procedure described in 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 (0.390 g) as a light yellow oil.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with a solvent gradient of from 0 to 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5becc4b519c34e6e876d4c3165e009ec
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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