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

HRID 1793987Notes

Reaction equation

HRID 1793987 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

Reactant 2

HCID 106349276,6-Dimethyl-1-cyclohexen-1-yl trifluoromethanesulfonateHCID 11235991Ethyl 4-(tributylstannyl)benzoate

Product 1

HCID 696525204-(6,6-Dimethyl-cyclohex-1-en-1-yl)-benzoic acid ethyl esterYield 69%

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

  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-56acc94ccb5f4520b28045c450296a2a
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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