Ethyl 4-(tributylstannyl)benzoate → 4-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-benzoic acid ethyl ester

HRID 1793996Notes

Reaction equation

HRID 1793996 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[CH:32]2[CH2:37][CH:34]([CH2:35][CH:36]=1)[C:33]2([CH3:39])[CH3:38])(=O)=O>>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:6]=[CH:7][C:8]([C:31]2[CH:32]3[CH2:37][CH:34]([CH2:35][CH:36]=2)[C:33]3([CH3:39])[CH3:38])=[CH:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 11235991Ethyl 4-(tributylstannyl)benzoateHCID 222196936,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl trifluoromethanesulfonate

Product 1

HCID 696525194-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-benzoic acid ethyl ester

Procedure

4-(Tri-n-butyl-stannyl)-benzoic acid ethyl ester of Example 15, Step A (1.45 g, 3.30 mmol) and 6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl trifluoromethanesulfonate (0.981 g, 3.63 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 crude title compound a 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-f5dd6a3dddde4d26861954402a0667da
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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