Picolinic acid → HCID 59563706, compound

HRID 1944148Notes

Reaction equation

HRID 1944148 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].I[C:10]1[CH:27]=[CH:26][C:13]([CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].N1C=CC=CC=1C(O)=O>O1CCOCC1.[Cu]I>[C:1]([CH:3]([C:10]1[CH:27]=[CH:26][C:13]([CH2:14][O:15][Si:16]([CH:20]([CH3:22])[CH3:21])([CH:23]([CH3:25])[CH3:24])[CH:17]([CH3:18])[CH3:19])=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 7764Ethyl cyanoacetateHCID 10796Cesium carbonateHCID 59563746HCID 59563746, compound

Product 1

HCID 59563706HCID 59563706, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 2-cyanoacetate and (4-iodobenzyloxy)triisopropylsilane (E199) in dioxane were added Cs2CO3, CuI, and picolinic acid. The mixture was stirred overnight at 90° C. The solid was removed by filtration and the dioxane concentrated under reduced pressure. Column chromatography (SiO2, hexane:ethyl acetate 25:1) gave pure ethyl 2-cyano-2-(4-((triisopropylsilyloxy)methyl)phenyl)acetate (E200) as a yellow oil.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe dioxane concentrated under reduced pressure

Sources & evidence

ORD record
ord-00385fd441024fb2b7a1be7af80fde47
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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