Ultrasound Assisted Synthesis of 5,9-Dimethylpentadecane and 5,9-Dimethylhexadecane – the Sex Pheromones of Leucoptera coffeella
Abstract
:Introduction
Results and Discussion
Conclusions
Acknowledgement
Experimental
General
General procedure for the tosylation of alcohols: 3,7-dimethyl-6-octenyl 4-methylbenzenesulfonate (4)
General procedure for the cross coupling reactions: 2,6-dimethyl-2-dodecene (5a)
General procedure for oxidation: 4-methyldecanal (6a)
General procedure for reduction: 4-methyl-1-decanol (7a)
References and Notes
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- The signals are separated from each other by Δδ = 0.002 ppm.
- Resolved resonances for the same carbon atom of two diastereomerically different forms.
- Sample Availability: Available from the authors.
Entry | 3 : TsCl : pyridine (molar ratios) | Time (minutes) | Yield of 4 (%) |
---|---|---|---|
1 | 1:1:1 | 30 | 82 |
2 | 1:1:1 | 60 | 83 |
3 | 1:1:2 | 30 | 86 |
4 | 1:1:2 | 60 | 84 |
5 | 1:1.5:1 | 60 | 80 |
6 | 1:1.5:2 | 30 | 91 |
7 | 1:1.5:2 | 20 | 84 |
8 | 1:1.5:2 | 40 | 92 |
9 | 1:1.5:3 | 30 | 92 |
10 | 1:2:2 | 20 | 86 |
11 | 1:2:2 | 30 | 92 |
Entry | Tosylate | Time (minutes) | Yield (%)a |
---|---|---|---|
1 | 8a | 30 | 74 |
2 | 8a | 45 | 92 |
3 | 8a | 60 | 93 |
4 | 8b | 30 | 78 |
5 | 8b | 45 | 91 |
6 | 8b | 60 | 91 |
Entry | Product | Time (minutes) | Yield (%)a |
---|---|---|---|
1 | 5a | 20 | 80 |
2 | 5a | 30 | 95 |
3 | 5a | 45 | 95 |
4 | 5b | 30 | 94 |
5 | 1 | 45 | 93 |
6 | 2 | 45 | 91 |
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Doan, N.N.; Le, T.N.; Nguyen, H.C.; Hansen, P.E.; Duus, F. Ultrasound Assisted Synthesis of 5,9-Dimethylpentadecane and 5,9-Dimethylhexadecane – the Sex Pheromones of Leucoptera coffeella. Molecules 2007, 12, 2080-2088. https://doi.org/10.3390/12082080
Doan NN, Le TN, Nguyen HC, Hansen PE, Duus F. Ultrasound Assisted Synthesis of 5,9-Dimethylpentadecane and 5,9-Dimethylhexadecane – the Sex Pheromones of Leucoptera coffeella. Molecules. 2007; 12(8):2080-2088. https://doi.org/10.3390/12082080
Chicago/Turabian StyleDoan, Nhuan Ngoc, Thach Ngoc Le, Hao Cong Nguyen, Poul Erik Hansen, and Fritz Duus. 2007. "Ultrasound Assisted Synthesis of 5,9-Dimethylpentadecane and 5,9-Dimethylhexadecane – the Sex Pheromones of Leucoptera coffeella" Molecules 12, no. 8: 2080-2088. https://doi.org/10.3390/12082080
APA StyleDoan, N. N., Le, T. N., Nguyen, H. C., Hansen, P. E., & Duus, F. (2007). Ultrasound Assisted Synthesis of 5,9-Dimethylpentadecane and 5,9-Dimethylhexadecane – the Sex Pheromones of Leucoptera coffeella. Molecules, 12(8), 2080-2088. https://doi.org/10.3390/12082080