Ethyl 4-(tributylstannyl)benzoate → 4-Bicyclo[3.2.1]oct-2-en-2-yl-benzoic acid ethyl ester

HRID 1793994Notes

Reaction equation

HRID 1793994 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[CH2:38][CH:35]([CH2:36][CH:37]=1)[CH2:34][CH2:33]2)(=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[CH2:38][CH:35]([CH2:36][CH:37]=2)[CH2:34][CH2:33]3)=[CH:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 11235991Ethyl 4-(tributylstannyl)benzoateHCID 22219695Bicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate

Product 1

HCID 696525294-Bicyclo[3.2.1]oct-2-en-2-yl-benzoic acid ethyl ester

Procedure

4-(Tri-n-butyl-stannyl)-benzoic acid ethyl ester of Example 15, Step A (1.82 g, 4.15 mmol) and bicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate (1.17 g, 4.57 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 10% 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 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2f69b3efc08249e3899a08f7df141a57
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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