Triethylamine → HCID 20728730, compound

HRID 722794Notes

Reaction equation

HRID 722794 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:9](OS(C(F)(F)F)(=O)=O)=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20].[Li+].[Cl-].[CH3:26][CH2:27]N(CC)CC.C([Sn](CCCC)(CCCC)C=C)CCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:9]([CH:26]=[CH2:27])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 20728729HCID 20728729, compound

Product 1

HCID 20728730HCID 20728730, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-methoxycarbonylmethyl-6-trifluoromethanesulfonyloxy-benzoic acid methyl ester (2.705 g, 7.6 mmol), LiCl (2.355 g, 55.6 mmol), NEt3 (1.5 mL, 10.8 mmol), Pd[P(C6H5)3]4 (1.09 g, 0.94 mmol), and tributyl (vinyl)tin (2.85 mL, 9.75 mmol) in dioxane (50 mL) was heated at reflux. After 3 h, the reaction was allowed to cool to rt, filtered through a pad of silica gel and concentrated. The crude product was purified by flash chromatography on SiO2 (13% EtOAc/hexanes) to afford 2-methoxycarbonylmethyl-6-vinyl-benzoic acid methyl ester as a yellow solid (1.50 g, 84%): 1H NMR (CDCl3) δ 3.67 (s, 3H), 3.89 (s, 5H), 5.32 (d, J=10.9 Hz, 1H), 5.68 (d, J=17.4 Hz, 1H) 6.82 (dd, J=17.4, 10.9 Hz, 1H), 7.20(d, J=7.1 Hz, 1H), 7.36(m, 1H), 7.50 (d, J=7.8 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. filtrationfiltered through a pad of silica gel
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on SiO2 (13% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b52edb7fcbc84f92865ec907c3da8bbf
Source dataset
uspto-grants-2006_11
Patent number
US07138543B2

Reaction notes

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