(5-Chloropyrazin-2-yl)methanol → Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate

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>>[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

Reactant 2

HCID 23462054(5-Chloropyrazin-2-yl)methanol

HCID 86603675Dioxane (carbethoxymethylene)triphenylphosphorane

Product 1

HCID 86603667Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylateYield 77.3%

Procedure

To a solution of (5-chloro-2-pyrazinyl)methanol (11.0 g) in dioxane (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

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

Sources & evidence

ORD record: ord-f3ed3b931f244fbf9b59a346da780e91
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465731B2

Reaction notes

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