ChemicalBook CAS DataBase List Methyl 4-oxobutanoate

Methyl 4-oxobutanoate synthesis

14synthesis methods

Product Name:Methyl 4-oxobutanoate
CAS Number:13865-19-5
Molecular formula:C5H8O3
Molecular Weight:116.12

35901-76-9 Synthesis

35901-76-9
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13865-19-5
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$45.00/50mg

Yield:13865-19-5 86%

Reaction Conditions:

Stage #1: methyl 5-methyl-hex-4-enoatewith ozone in methanol;dichloromethane at -78; for 0.5 h;
Stage #2: with triphenylphosphine in methanol;dichloromethane at -78 - 20; for 3 h;

Steps:

Methyl 4-oxobutanoate (5)

A solution of S2 (12.0 g, 84.3 mmol) in the 5:1 mixture of CH₂Cl₂ and MeOH (total 120 mL) was stirred under O₃bubbling for 30 minutes at -78 °C. Then the reaction mixture was bubbled with argon gas to purge off unreacted O₃, and triphenyl phosphine (26.5 g, 101 mmol) was added at -78 °C. The resulting mixture was stirred at room temperature for 3 hours. Then the reaction mixture was concentrated by distillation. The resulting residue was purified by distillation (75 °C, 15 mmHg) to afford 51 (8.46 g, 86%) as a colorless oil.

References:

Ishikawa, Ryo;Yoshida, Naoto;Akao, Yusuke;Kawabe, Yusuke;Inai, Makoto;Asakawa, Tomohiro;Hamashima, Yoshitaka;Kan, Toshiyuki [Chemistry Letters,2014,vol. 43,# 10,art. no. CL-140613,p. 1572 - 1574] Location in patent:supporting information

1490-25-1 Synthesis