Methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-cyanomethoxy-acrylate → Methyl 2-(2-hydroxyphenyl)-3-cyanomethoxy-acrylate
Reaction equation
O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[CH:19][O:20][CH2:21][C:22]#[N:23])[C:15]([O:17][CH3:18])=[O:16]>CO>[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[CH:19][O:20][CH2:21][C:22]#[N:23])[C:15]([O:17][CH3:18])=[O:16]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of 14.4 g (45.3 mmol) of methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-cyanomethoxy-acrylate in 50 ml of methanol is admixed with 5 g of acidic ion exchanger and stirred at 20° C. for 3 hours. The ion exchanger is filtered off and the filtrate is concentrated under reduced pressure. The residue is chromatographed over silica gel using dichloromethane/ethyl acetate (10:1). 7.8 g (74% of theory) of methyl 2-(2-hydroxyphenyl)-3-cyanomethoxy-acrylate are obtained.
Workup
- filtrationThe ion exchanger is filtered off
- concentrationthe filtrate is concentrated under reduced pressure
- customThe residue is chromatographed over silica gel
Sources & evidence
- ORD record
- ord-54e17a3472274ee8bc065a89ebbda14e
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977123
Reaction notes
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