Chloroacetonitrile → Methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-cyanomethoxy-acrylate
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[CH2:19])[C:15]([O:17][CH3:18])=[O:16].[H-].[Na+].[C:22](=[O:25])([O-])[O-].[K+].[K+].ClC[C:30]#[N:31]>C(OC)=O.CN(C)C=O.O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[CH:19][O:25][CH2:22][C:30]#[N:31])[C:15]([O:17][CH3:18])=[O:16]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 20 °C
Procedure
At 20° C., a solution of 15 g (60 mmol) of methyl 2-[2-(tetrahydropyran-2-yloxy)phenyl]-acrylate in 36 ml of methyl formate is added dropwise to a suspension of 1.96 g (66 mmol) of sodium hydride (80% strength) in 50 ml of dimethylformamide. After 4 hours, 15 g of potassium carbonate and 9 g of chloroacetonitrile are added to this mixture, which is stirred at 20° C. for a further 14 hours and then poured into water. The reaction mixture is extracted with ethyl acetate and the organic phase is dried over sodium sulphate and concentrated under reduced pressure. 15.9 g (83.55% of theory) of methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-cyanomethoxy-acrylate are obtained.
Workup
- extractionThe reaction mixture is extracted with ethyl acetate
- dry with materialthe organic phase is dried over sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8c93fcd0ef4b41a38a480ea3997a7be6
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977123
Reaction notes
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