cyclohexanecarboxylic acid, 1-cyano-, ethyl ester synthesis
- Product Name:cyclohexanecarboxylic acid, 1-cyano-, ethyl ester
- CAS Number:1130-21-8
- Molecular formula:C10H15NO2
- Molecular Weight:181.23
111-24-0
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1130-21-8
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Yield:1130-21-8 77.2%
Reaction Conditions:
with Cs2CO3
Steps:
37.1 Step 1:
Step 1:
Synthesis of (1-(aminomethyl)cyclohexyl)methanol
Ethyl 2-cyanoacetate (5.377 mL, 50.389 mmol) was dissolved in N,N-dimethylformamide (200 mL), and cesium carbonate (Cs2CO3, 41.044 g, 125.972 mmol) and 1,5-dibromopentane (6.816 mL, 50.389 mmol) was added thereto at 0° C., followed by stirring at the same temperature for 30 minutes and further stirring at room temperature for 12 hours.
Water was poured into the reaction mixture, followed by extraction with ethyl acetate.
The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain ethyl 1-cyanocyclohexane-1-carboxylate (7.050 g, 77.2%, colorless liquid).
To the solution in which the obtained product was dissolved in tetrahydrofuran (200 mL) at 0° C., lithium aluminum hydride (2.40 M solution in THF, 43.681 mL, 104.833 mmol) was added, and the reaction mixture was stirred at room temperature for 3 hours.
References:
US2022/274939,2022,A1
