2-(p-Nitrophenyl)acetoacetic acid ethyl ester synthesis
- Product Name:2-(p-Nitrophenyl)acetoacetic acid ethyl ester
- CAS Number:10565-18-1
- Molecular formula:C12H13NO5
- Molecular Weight:251.24
Yield:10565-18-1 43%
Reaction Conditions:
with potassium phosphate;palladium diacetate;XPhos in toluene at 90; for 16 h;Inert atmosphere;
Steps:
301 Preparation 301 Ethyl 2-(4-nitrophenyl)-3-oxobutanoate
To a stirred solution of l-chloro-4-nitrobenzene in toluene was added ethyl 3-oxobutanoate and K3PO4 at room temperature. The resulting reaction mixture was purged with argon gas for 15 min and then Pd(OAc)2 and X-phos were added. The reaction mixture was stirred at 90°C for 16 hours then filtered through a Celite pad and washed with EtOAc (100 ml_). The filtrate was concentrated under reduced pressure and the crude product was purified by silica gel (100-200 mesh) column chromatography (10% EtOAc in hexane as eluent) to afford the title compound (3.5 g, 43%) as a brown oil. 1H NMR (400 MHz, DMSO-d6) d 8.26-8.18 (m, 2H), 7.62-7.51 (m, 2H), 4.20-4.02 (m, 3H), 2.22 (s, 3H), 1.26-1.18 (m, 3H); LCMS (METHOD 5) (ESI) : m/z: 250 [M-H]; RT=3.95 min; (ACQUITY BEH C18 column, 0.1% FA in water with MeCN).
References:
WO2020/127685,2020,A1 Location in patent:Page/Page column 162
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