Lithium Chloride → Ethyl [3-(pyridin-3-yl)phenyl]acetate

HRID 1494137Notes

Reaction equation

HRID 1494137 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=1)(=O)=O.C[Sn](C)C.C[Sn](C)C.FC(F)(F)S(O[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)(=O)=O.[Cl-].[Li+]>O1CCOCC1.CCOCC.[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>[N:37]1[CH:38]=[CH:39][CH:40]=[C:35]([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=2)[CH:36]=1

Participants

8

Reactant 4

HCID 433294Lithium ChlorideHCID 6327618HexamethylditinHCID 110315793-Pyridyl TrifluoromethanesulfonateHCID 14986694HCID 14986694, compound

Product 1

HCID 14986695Ethyl [3-(pyridin-3-yl)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2.04 g (6.5 mmol) of ethyl m-(trifluoromethanesulfonyloxy)phenylacetate in 33 mL dioxane is added 1.33 mL (6.5 mmol) hexamethylditin followed by 1.49 g (6.6 mmol) 3-(trifluoromethanesulfonyloxy)-pyridine, 0.827 g (19.5 mmol) lithium chloride and 0.15 g (0.13 mmol) tetrakis-(triphenylphosphine) palladium(0). The mixture is then heated at 90° C. for 62 hours, diluted with ether and washed with 10% ammonium hydroxide followed by water and brine. The organic layer is dried, filtered, evaporated and the residue is purified by flash chromatography using 1:1 ether and hexane as eluent to give ethyl m-(3-pyridyl)phenylacetate; IR (CH2Cl2) 1731 cm-1.

Workup

  1. washwashed with 10% ammonium hydroxide
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-4683e9a3b3364fceb1397758c537615f
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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