4-Propionyl-2-propylphenyl 1,1,1-trifluoromethanesulfonate → 6-Methyl-4'-propionyl-2'-propylbiphenyl-3-carbaldehyde

HRID 584315Notes

Reaction equation

HRID 584315 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:9][C:8]=1[CH2:17][CH2:18][CH3:19])(=O)=O.[O:22]1CCO[CH:23]1[C:27]1[CH:28]=[CH:29][C:30]([CH3:36])=[C:31](B(O)O)[CH:32]=1>>[CH3:36][C:30]1[C:29]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:9][C:8]=2[CH2:17][CH2:18][CH3:19])=[CH:28][C:27]([CH:23]=[O:22])=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 223456254-Propionyl-2-propylphenyl 1,1,1-trifluoromethanesulfonateHCID 223456365-[1,3]Dioxolan-2-yl-2-methylphenylboronic acid

Product 1

HCID 223456266-Methyl-4'-propionyl-2'-propylbiphenyl-3-carbaldehyde

Procedure

In a manner similar to that of Example 1(g), by reacting 2 g (6.2 mmol) of 4-propionyl-2-propylphenyl 1,1,1-trifluoromethanesulfonate with 1.2 g (8 mmol) of 5-[1,3]dioxolan-2-yl-2-methylphenylboronic acid, and after purification by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (90/10), 1.42 g (78%) of product are obtained in the form of a pale yellow oil.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a mixture of heptane and ethyl acetate (90/10), 1.42 g (78%) of product
  3. customare obtained in the form of a pale yellow oil

Sources & evidence

ORD record
ord-27c682af5a7f4db8be1ffad8299960ae
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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