Triethylamine → HCID 20728725, compound

HRID 1352824Notes

Reaction equation

HRID 1352824 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=2)[C:8]=1[C:23]([O:25][CH3:26])=[O:24])(=O)=O.[Li+].[Cl-].[CH2:31](N(CC)CC)[CH3:32].C([Sn](CCCC)(CCCC)C=C)CCC>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:31]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=2)[C:8]=1[C:23]([O:25][CH3:26])=[O:24])=[CH2:32]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 20728724HCID 20728724, compound

Product 1

HCID 20728725HCID 20728725, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-trifluoromethanesulfonyloxy-[1,1′-biphenyl]-2,3′-dicarboxylic acid, dimethyl ester (1.3 g, 3.1 mmol), tetrakis (triphenylphosphine) palladium (0.36 g, 0.31 mmol), LiCl (0.94 g, 22.2 mmol), triethylamine (0.6 mL, 4.3 mmol) and tri-n-butyl(vinyl)tin (1.0 mL, 3.4 mmol) in 1,4-dioxane (30 mL) was heated at reflux under N2 for 4 hours. After cooling to room temperature, the mixture was filtered through a plug of silica gel and the filtrate was concentrated. Purification by flash chromatography (1:10 EtOAc/hexanes) provided 3-ethenyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid, dimethyl ester (0.91 g, 99%) as a white solid: 1H NMR (CDCl3) δ3.61 (s, 3H), 3.92 (s, 3H), 5.40 (d, J=11.1 Hz, 1H), 5.79 (d, J=17.5 Hz, 1H), 6.87 (dd, J=17.4, 11.0 Hz, 1H), 7.31 (d, J=7.5 Hz, 1H), 7.44-7.49 (m, 2H), 7.56 (dm, J=7.5 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 8.03 (dm, J=7.5 Hz, 1H), 8.08 (t, 1, J=1.5 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 4 hours
  3. filtrationthe mixture was filtered through a plug of silica gel
  4. concentrationthe filtrate was concentrated
  5. customPurification by flash chromatography (1:10 EtOAc/hexanes)

Sources & evidence

ORD record
ord-337829790b444f57ae4194278400decf
Source dataset
uspto-grants-2007_05
Patent number
US07220780B2

Reaction notes

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