Methyl 4-methoxyacetoacetate synthesis
- Product Name:Methyl 4-methoxyacetoacetate
- CAS Number:41051-15-4
- Molecular formula:C6H10O4
- Molecular Weight:146.14
Methyl 4-methoxyacetoacetate is used as a pharmaceutical and pesticide intermediate, mainly in the synthesis of dolutegravir sodium. It can be synthesized by the condensation reaction of Methyl 4-chloro-3-oxo-butanoate and Methanol.
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41051-15-4
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Yield:41051-15-4 93%
Reaction Conditions:
Stage #1:methanol with sodium hydride in tetrahydrofuran at 20;
Stage #2:Methyl 4-chloroacetoacetate in tetrahydrofuran at 20;
Steps:
General procedure h (adapted from S. Mitsuhashi et al, J. Am. Chem. Soc. 2008, 130, 4140).
General procedure: To a suspension of sodium hydride (2.2 eq) in THF (0.5 M) at RT, an alcohol (1.1 eq) was added dropwise. The mixture was stirred for 5 min before methyl 4-chloro-3-oxobutanoate (1 eq) was dropwise added. This mixture was stirred for 30 min and then concentrated in vacuum. Water was added, and the pH was adjusted to 6-7 by the addition of 2N aq. HCl. The resulting mixture was extracted with dichloromethane (×2) and ethyl acetate (×2), and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash column chromatography on silica gel using ethyl acetate/hexane as eluent to afford the corresponding dicarbonyl compound.
References:
Oncostellae, S.L.;KURZ, Guido;CAMACHO GóMEZ, Juan EP3480201, 2019, A1 Location in patent:Paragraph 0288; 0289; 0291; 0292
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41051-15-4
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41051-15-4
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