(4-Nitrophenyl)methyl 3-oxobutanoate synthesis
- Product Name:(4-Nitrophenyl)methyl 3-oxobutanoate
- CAS Number:61312-84-3
- Molecular formula:C11H11NO5
- Molecular Weight:237.21
674-82-8
619-73-8
61312-84-3
GENERAL STEPS: 4-Nitrobenzyl alcohol (1.53 g, 10 mmol) was placed in a round bottom flask and dichloromethane (10 mL) was added. Bis(vinylidene) ketone (1.26 g, 15 mmol) was slowly added followed by triethylamine (0.14 mL, 1 mmol) under cooling in an ice bath. The reaction mixture was warmed up to room temperature with continuous stirring for 3 hours. Upon completion of the reaction, it was quenched by the addition of water (10 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 4-nitrobenzyl acetoacetate (2.30 g, 97% yield). Referring to the method of Example 1, the resulting 4-nitrobenzyl acetoacetate was further reacted to produce ethyl p-nitrobenzyl acetoacetate (2.09 g, 68% yield). The structure of the product was confirmed by 1H NMR (CDCl3) and mass spectrum: 1H NMR (CDCl3) δ 8.25 (d, 2H), 7.53 (s, 1H), 7.51 (d, 2H), 6.57 (s, 1H), 5.27 (s, 2H), 4.21 (s, 2H), 2.54 (s, 3H); MS (M+1): 308.
Yield:61312-84-3 97%
Reaction Conditions:
with triethylamine in dichloromethane at 0 - 20; for 3 h;
Steps:
2 Example 2; Synthesis of 6-methyl-2-thioxo-l,2,3,4-tetrahydro-pyrimidine-5-carboxylicacid 4-nitro-benzyl ester (7)
4-Nitrobenzyl alcohol (1.53 g, 10 mmol) was introduced into a round bottomedflask, and dichloromethane (10 mNo. ) was added thereto. After the solution was cooledusing an ice bath, diketene (1.26 g, 15 mmol) was slowly added, and triethyknine(0.14 m-6 , 1 mmol) was added. This solution was warmed to room temperature, stirredfor 3 hours, and water (10 m-6 ) was added. The organic kyer was dried over MgSOand distilled under reduced pressure to give 4-nitrobenzyl acetoacetate (2.30 g,Yield=97%). The resulting 4-nitrobenzyl acetoacelate was reacted according to thesame procedure as Example 1 to give the title compound in the yield of 68% (2.09 g).1 H NMR(CDC1): 5 8.25(d, 2H), 7.53(s, 1H), 7.5l(d, 2H), 6.57(s, 1H), 5.27(s,32H), 4.21(s, 2H), 2.54(s, 3H)MS(M+1): 308
References:
WO2004/111013,2004,A1 Location in patent:Page 39-40
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