Ethyl 2-oxocyclohexanecarboxylate synthesis
- Product Name:Ethyl 2-oxocyclohexanecarboxylate
- CAS Number:1655-07-8
- Molecular formula:C9H14O3
- Molecular Weight:170.21
108-94-1
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105-58-8
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1655-07-8
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Yield:1655-07-8 80%
Reaction Conditions:
Stage #1: Diethyl carbonatewith sodium hydride in tetrahydrofuran; for 1 h;Reflux;
Stage #2: cyclohexanone in tetrahydrofuran; for 2 h;Reflux;
Steps:
1 Ethyl 2-oxocyclohexanecarboxylate
A 1000 mL flashk was charged with diethyl carbonate (146 mL, 1.2 mol) and 150 mL of dry THF, and NaH (60%, 63 g, 1.6 mol) was added to the mixtrure under stirring. The mixture was heated to reflux for 1 h, and then, a solution of cyclohexanone (50 mL, 0.48 mol) in anhydrous THF (50 mL) was added dropwise to the mixture, and the addition of cyclohexanone was continued for ca. 0.5 h. The mixture was refluxed for an additional 1.5 h. After cooled, the mixture was hydrolyzed by 3N hydrochloric acid, then poured into brine, extracted by DCM (75 mLx3). The combined organic layer was dried and evaporated to give the title compound (66 g, 80% yield) as brown oil which was set to do next step without any purification. MS: m/z 171.3 [M+H]+.
References:
WO2013/64083,2013,A1 Location in patent:Page/Page column 23
17605-06-0
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1655-07-8
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2050-20-6
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1655-07-8
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623-73-4
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120-92-3
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1655-07-8
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55718-61-1
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1655-07-8
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$6.00/5g