Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Experimental
2.2. General Procedure for the Synthesis of α-Hydroxyphosphonates 2
2.3. General Procedure for the Synthesis of Phosphates 3 from α-Hydroxyphosphonates 2
2.4. General Procedure for the Synthesis of Phosphates 3 from Aromatic Aldehydes and Phosphites
3. Results and Discussion
3.1. Pudovik Reaction
3.2. Phospha-Brook Rearrangement
3.3. One-Pot Pudovik–Phospha-Brook Rearrangement
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry a | DBN (mol%) | Stirring Rate (rpm) | Temperature (°C) | tres (min) | 1b | NMR Yield b (%) 2b | 3b |
---|---|---|---|---|---|---|---|
1 | 5 | 500 | 40 | 20 | 22 | 44 | 34 |
2 | 5 | 500 | 40 | 120 | 4 | 48 | 48 |
3 | 5 | 500 | 60 | 20 | 12 | 51 | 37 |
4 | 5 | 500 | 25 | 20 | 32 | 63 | 5 |
5 | 5 | 500 | 25 | 60 | 29 | 65 | 6 |
6 | 5 | 500 | 25 | 90 | 15 | 78 | 7 |
7 | 5 | 500 | 25 | 120 | 5 | 88 | 7 |
8 | 5 | 500 | 25 | 180 | 10 | 79 | 11 |
9 | 5 | 250 | 25 | 120 | 16 | 75 | 9 |
10 | 5 | 1000 | 25 | 120 | 13 | 74 | 13 |
11 | 2.5 | 500 | 25 | 120 | 34 | 60 | 6 |
12 | 1 | 500 | 25 | 120 | 46 | 52 | 2 |
Entry a | Stirring Rate (rpm) | Temperature (°C) | tres (min) | NMR Yield b (%) |
---|---|---|---|---|
1 | 500 | 25 | 30 | 20 |
2 | 500 | 25 | 60 | 50 |
3 | 500 | 25 | 120 | 94 |
4 | 500 | 25 | 150 | 92 |
5 | 250 | 25 | 120 | 29 |
6 | 1000 | 25 | 120 | 63 |
7 | 1500 | 25 | 120 | 37 |
8 | 500 | 40 | 120 | 90 |
9 | 500 | 50 | 120 | 83 |
10 | 500 | 60 | 120 | 84 |
11 c | 500 | 25 | 120 | 87 |
Entry a | DBN (equiv) | Stirring Rate (rpm) | Temperature (°C) | tres (min) | NMR Yield b (%) |
---|---|---|---|---|---|
1 | 0.1 | 500 | 40 | 120 | 47 |
2 | 0.1 | 500 | 40 | 180 | 79 |
3 | 0.2 | 500 | 40 | 180 | 80 |
4 | 0.5 | 500 | 40 | 180 | 82 |
5 | 1 | 500 | 40 | 180 | 85 |
6 | 1 | 500 | 40 | 120 | 90 |
7 | 1 | 500 | 25 | 120 | 90 |
8 | 1 | 500 | 25 | 60 | 71 |
9 | 1 | 1000 | 25 | 120 | 88 |
10 | 1 | 250 | 25 | 120 | 83 |
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Dean, J.; Buckler Reinoso, N.; Spiedo, F.; Romero Fernández, C.; Patel, B. Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN. Reactions 2024, 5, 812-822. https://doi.org/10.3390/reactions5040042
Dean J, Buckler Reinoso N, Spiedo F, Romero Fernández C, Patel B. Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN. Reactions. 2024; 5(4):812-822. https://doi.org/10.3390/reactions5040042
Chicago/Turabian StyleDean, Joseph, Natalia Buckler Reinoso, Francesco Spiedo, Carola Romero Fernández, and Bhaven Patel. 2024. "Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN" Reactions 5, no. 4: 812-822. https://doi.org/10.3390/reactions5040042