ChemicalBook CAS DataBase List 2-(p-Nitrophenyl)acetoacetic acid ethyl ester

2-(p-Nitrophenyl)acetoacetic acid ethyl ester synthesis

4synthesis methods

Product Name:2-(p-Nitrophenyl)acetoacetic acid ethyl ester
CAS Number:10565-18-1
Molecular formula:C12H13NO5
Molecular Weight:251.24

141-97-9 Synthesis

141-97-9
796 suppliers
$5.00/25g

100-00-5
12 suppliers
$14.14/5gm:

2-(p-Nitrophenyl)acetoacetic acid ethyl ester

10565-18-1
0 suppliers
inquiry

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

141-97-9 Synthesis

141-97-9
796 suppliers
$5.00/25g

350-46-9 Synthesis