Ethyl orthoformate → (2Z)-2-(Ethoxymethylene)-3-oxobutanenitrile
Reaction equation
[O:1]=[C:2]([CH3:6])[CH2:3][C:4]#[N:5].[CH:7](OCC)(OCC)[O:8][CH2:9][CH3:10]>C(OC(=O)C)(=O)C>[CH2:9]([O:8]/[CH:7]=[C:3](\[C:2](=[O:1])[CH3:6])/[C:4]#[N:5])[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
Into a round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-oxobutanenitrile (compound 257.1, 16.0 g, 193 mmol) in acetic anhydride (48 mL). Triethyl orthoformate (96 mL, 577 mmol) was added and the reaction was stirred for 2 h at 130° C., then concentrated under reduced pressure to obtain the title compound as a red solid (10 g, 37%).
Workup
- customInto a round-bottom flask, which was purged
- temperaturemaintained with an inert atmosphere of nitrogen
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-36cd76d4f8754555b6dc57c789c5b017
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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