Methyl 4-oxobutanoate synthesis
- Product Name:Methyl 4-oxobutanoate
- CAS Number:13865-19-5
- Molecular formula:C5H8O3
- Molecular Weight:116.12
35901-76-9
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13865-19-5
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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 O3 bubbling 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
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13865-19-5
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925-57-5
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13865-19-5
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818-57-5
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13865-19-5
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4220-66-0
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13865-19-5
165 suppliers
$45.00/50mg