Water → 2-Fluoro-4-methoxy-6-(tetrahydro-furan-3-yloxy)-benzonitrile
Reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:8][CH2:7][O:6][CH2:5]1.[F:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14](F)[C:11]=1[C:12]#[N:13].O>O1CCCC1>[F:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:3][CH:4]2[CH2:8][CH2:7][O:6][CH2:5]2)[C:11]=1[C:12]#[N:13]Participants
Procedure
Sodium hydride (60% in mineral oil, 0.83 g, 21 mmol) was added portionwise to 3-hydroxytetrahydrofuran (1.82 g, 21 mmol) in tetrahydrofuran (40 ml) at 0° C. under a nitrogen atmosphere. The suspension was warmed to room temperature and was stirred for 1 hour. The mixture formed was added over 30 minutes to 2,6-difluoro-4-methoxy-benzonitrile (Mol. Cryst. Liq. Cryst. 1989, 172) (3.5 g, 21 mmol) in tetrahydrofuran (50 ml) and the resulting solution was held at room temperature for 16 hours. Water (75 ml) was added and the aqueous mixture was extracted with ethyl acetate (3×200 ml) The combined organic solutions were dried over magnesium sulphate and evaporated under reduced pressure. The material obtained was dried under vacuum to give the title compound as a brown solid (5.1 g).
Workup
- customThe mixture formed
- waitthe resulting solution was held at room temperature for 16 hours
- extractionthe aqueous mixture was extracted with ethyl acetate (3×200 ml) The combined organic solutions
- dry with materialwere dried over magnesium sulphate
- customevaporated under reduced pressure
- customThe material obtained
- customwas dried under vacuum
Sources & evidence
- ORD record
- ord-1687b12d04cb4af381b02b3cddc1df3e
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06936619B2
Reaction notes
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