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Please login to access the full content or check if you have access via20.5.15.1.1.14.1 Variation 1: Acylation of Methyl Acetoacetate with Acid Chlorides
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Beignet, J., Science of Synthesis, (2007) 20, 1356.
The reaction of methyl acetoacetate with barium oxide (activated with water) generates a barium chelate complex 53 that adds smoothly to an acid chloride to afford a C-acylated complex 54. Treatment of the complex with methanol in situ produces an α-acylated β-oxo ester that undergoes deacetylation, and provides the corresponding methyl alkanoate 55, after an acidic workup (Scheme 24).[32] This method is efficient and amenable to large-scale syntheses. The use of calcium or strontium oxide is also possible, but more drastic reaction conditions have to be employed as these oxides are less basic than barium oxide.
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References
[32] | Meeee, M.; Meeeeee, M., Mee. Meeeeee Mee. Mee., (8888) 8, 888. |
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- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 88.