Ethyl 4-(tributylstannyl)benzoate → 4-(6-tert-Butyl-cyclohex-1-en-1-yl)-benzoic acid ethyl ester

HRID 1793993Notes

Reaction equation

HRID 1793993 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:36]([C:37]([CH3:40])([CH3:39])[CH3:38])[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[CH:36]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:31][CH2:32][CH2:33][CH:34]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 11235991Ethyl 4-(tributylstannyl)benzoateHCID 158824046-Tert-butyl-cyclohex-1-en-1-yl trifluoromethanesulfonate

Product 1

HCID 696526284-(6-tert-Butyl-cyclohex-1-en-1-yl)-benzoic acid ethyl esterYield 66.8%

Procedure

4-(Tri-n-butyl-stannyl)-benzoic acid ethyl ester of Example 15, Step A (2.00 g, 4.55 mmol) and 6-tert-butyl-cyclohex-1-en-1-yl trifluoromethanesulfonate (1.43 g, 5.01 mmol) were reacted by the procedure described in 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 followed by recrystallization from methanol (0° C.) afforded the title compound (0.870 g) as white crystals, m.p. 50° C.

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
  3. customfollowed by recrystallization from methanol (0° C.)

Sources & evidence

ORD record
ord-229b4d201b5a4e3eb2147f88319f7f3d
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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