Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate

HRID 226369Notes

Reaction equation

HRID 226369 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.[C:10]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13][CH3:14])=[O:11]>O1CCOCC1.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:15]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 23462054(5-Chloropyrazin-2-yl)methanol

Product 1

HCID 86603667Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylateYield 68%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (5-chloro-2-pyrazinyl)methanol (11.0 g) in dioxane (110 mL) was added manganese(IV) oxide (26.5 g) and (carbethoxymethylene)triphenylphosphorane (29.2 g). After stirring for 2 hours at room temperature, a resulting precipitate was filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (11.0 g).

Workup

  1. filtrationa resulting precipitate was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-173024c0d56d4d938e1e05aa7b42dc11
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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