Recent insights (1) in the remarkable solvent properties of dimethyl eulfoxida (DMSO), and our own interest in the chemistry of isopropcnyl ethers (2) led u8 to consider the poraibility of direot 0-alkylation of ethyl aoetoaoetate in that solvent. The connection i# that Kornblum'rr work (3) suggests
Oxygen alkylation in the ethyl acetoacetate synthesis
✍ Scribed by G. Brieger; W.M. Pelletier
- Publisher
- Elsevier Science
- Year
- 1965
- Tongue
- French
- Weight
- 163 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
In a search for convenient preparative techniques, we have investigated the effect of solvent, halide, base, and temperature on the alkylation of the ambldent anion derived from ethyl acetoacetate. Our attention has focused on the use of dipolar aprotic solvents. A recent report (1) describing oxygen al&-lation in small yield using the standard synthesis (2) prompts us to report our findings.
📜 SIMILAR VOLUMES
retarding effect of alkali metal and alkaline-earth metal ions on the rate of intramolecular 0-alkylation of the title compound has been thoroughly investigated in 99% aqueous Me2SO at 25-C. Rate data have been dissected into contributions of free ions (ki) and ion pairs (k. ). Xl Comparison of the
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## Abstract In Simonis reaction with ethyl acetoacetate naphthalene‐2,6‐diol gives 8‐hydroxy‐3‐methyl‐1H‐naphtho[2,1‐b]‐pyran‐1‐one and naphthalene‐2,7‐diol gives the related 9‐hydroxy isomer. In Pechman reactions, the former diol yields a coumarin, 8‐hydroxy‐1‐methyl‐3H‐naphtho[2,1‐b]‐pyran‐3‐one,