Toluene → 3-(Allyloxy)-6-fluoro-2-pyrazinecarbonitrile

HRID 392359Notes

Reaction equation

F[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([F:8])=[CH:6][N:7]=1.[CH2:11]([OH:14])[CH:12]=[CH2:13].C(N(CC)CC)C.C1(C)C=CC=CC=1>CS(C)=O.O>[CH2:11]([O:14][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([F:8])=[CH:6][N:7]=1)[CH:12]=[CH2:13]

Participants

Conditions

Temperature: 60 °C

Procedure

In 30 mL of dimethyl sulfoxide was dissolved 10.0 g of 3,6-difluoro-2-pyrazinecarbonitrile. After adding 50 mL of allyl alcohol and 14.8 mL of triethylamine successively, the mixture thus obtained was stirred at 60° C. for 40 minutes. The reaction mixture was cooled to room temperature and poured into a mixture of 50 mL of toluene and 50 mL of water, and the organic layer was separated. The organic layer thus obtained was washed successively with ten 50 mL portions of water and then with saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=10:1] to obtain 11.5 g of 3-(allyloxy)-6-fluoro-2-pyrazinecarbonitrile as a light yellow-colored oily product.

Workup

customthe mixture thus obtained
temperatureThe reaction mixture was cooled to room temperature
customthe organic layer was separated
customThe organic layer thus obtained
washwas washed successively with ten 50 mL portions of water
dry with materialwith saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue thus obtained
customwas purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=10:1]

Sources & evidence

ORD record: ord-ebef546e933145dbb351720fa0f334a3
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800629B2

Reaction notes

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