Triethylamine → HCID 68227270, compound

HRID 403244Notes

Reaction equation

HRID 403244 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5](I)=[N:6][CH:7]=1.[C]=O.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])C.C(N(CC)CC)C>C(O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl.[Pd](Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([C:18]([O:21][CH2:22][CH3:23])=[O:20])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86670906HCID 86670906, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 68227270HCID 68227270, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 702EthanolSolvent

Procedure

Ethyl 2-(5-chloro-2-iodopyridin-3-yloxy)acetate (16.5 g, 48.3 mmol) was carbonylated with 20 bar carbon monoxide in the presence of bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct (1.66 g, 2.03 mmol) in a mixture of ethanol, ethyl acetate and triethylamine at 70° C. for 20 h. The crude reaction mixture was extracted with ethyl acetate and water, the organic layer was dried over sodium sulfate. Removal of the solvent in vacuum left a dark brown oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the ethyl 5-chloro-3-(2-ethoxy-2-oxoethoxy)picolinate (12.5 g, 43.4 mmol, 89.9% yield) as a light red solid. MS (ISP): m/z=287.9 [(M+H)+] and 290.1 [(M+2+H)+].

Workup

  1. customThe crude reaction mixture
  2. extractionwas extracted with ethyl acetate and water
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customRemoval of the solvent in vacuum
  5. waitleft a dark brown oil, which
  6. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-8f5972dc18ef44d6b28d69c5be59b16a
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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