1-Cyclohexenyl trifluoromethanesulfonate → HCID 69652551, compound

HRID 1794000Notes

Reaction equation

HRID 1794000 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][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:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=2)=[C:6]([CH3:19])[CH:5]=1

Participants

3

Reactant 2

HCID 3194401-Cyclohexenyl trifluoromethanesulfonateHCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester

Product 1

HCID 69652551HCID 69652551, compoundYield 95.2%

Procedure

3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Step A (5.00 g, 18.1 mmol) and cyclohex-1-en-1-yl trifluoromethanesulfonate (4.58 g, 19.9 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with 10% ethyl acetate in hexane, afforded the title compound (3.97 g) as a clear oil.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-dc5f526906d449d1bc84782925e2c0c3
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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