Synthesis of γ-Nitro Aliphatic Methyl Esters Via Michael Additions Promoted by Microwave Irradiation
Abstract
:1. Introduction
2. Results and Discussion
2.1. Preparation of methyl 3-methyl-4-nitrobutanoate (3)
Entry | Eq. DBU | Power (W) | Temperature (oC) | Time (min) | Yield 3 (%) |
---|---|---|---|---|---|
1 | 1.1 | - | r. t. | 4320 | 72 |
7 | 0.01 | 50 | 70-75 | 5 | 10 c |
2.2. Preparation of methyl 4-nitrobutanoate (5) and methyl 2-methyl-4-nitrobutanoate (8)
Entry | Eq. Base | Power (W) | Temperature (oC) | Time (min) | 8 / 9 / 7 (%) a |
---|---|---|---|---|---|
1 | 1.1 DBU | - | r. t. | 4320 | 47 / 53 / 0 |
2.3. Preparation of methyl 3-methy-4-nitropentanoate (11), methyl 4-nitropentanoate (12), and methyl 2-methy-4-nitropentanoate (13)
Entry | Methyl acrylates | Eq. DBU | Power (W) | Temperature (oC) | Time (min) | Product (%) a |
---|---|---|---|---|---|---|
1 | 1 | 0.05 | 50 | 70-75 | 5 | 11 (98) b |
3. Conclusions
4. Experimental
4.1. General
4.2. General procedure: Synthesis of methyl 4-nitro alkyl esters via microwave irradiation
Acknowledgements
References and Notes
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Escalante, J.; Díaz-Coutiño, F.D. Synthesis of γ-Nitro Aliphatic Methyl Esters Via Michael Additions Promoted by Microwave Irradiation. Molecules 2009, 14, 1595-1604. https://doi.org/10.3390/molecules14041595
Escalante J, Díaz-Coutiño FD. Synthesis of γ-Nitro Aliphatic Methyl Esters Via Michael Additions Promoted by Microwave Irradiation. Molecules. 2009; 14(4):1595-1604. https://doi.org/10.3390/molecules14041595
Chicago/Turabian StyleEscalante, Jaime, and Francisco D. Díaz-Coutiño. 2009. "Synthesis of γ-Nitro Aliphatic Methyl Esters Via Michael Additions Promoted by Microwave Irradiation" Molecules 14, no. 4: 1595-1604. https://doi.org/10.3390/molecules14041595