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CAS RN: 16139-79-0 | Product Number: D2547
Ethyl Diphenylphosphonoacetate [Horner-Emmons Reagent]
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![Ethyl Diphenylphosphonoacetate [Horner-Emmons Reagent]](/_ui/responsive/theme-tci/images/missing_product_zoom.jpg "Ethyl Diphenylphosphonoacetate [Horner-Emmons Reagent]")
Purity: >96.0%(GC)
Synonyms:
- Diphenylphosphonoacetic Acid Ethyl Ester
Product Documents:
| Size | Unit Price | Same Day | 2-3 Business Days | Other Lead Time |
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|---|---|---|---|---|---|
| 1G |
$209.00
|
1 | 0 | It can be shipped in about 5-6 months after ordering | |
| 5G |
$602.00
|
2 | 2 | It can be shipped in about 5-6 months after ordering |
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| Product Number | D2547 |
| Purity / Analysis Method | >96.0%(GC) |
| Molecular Formula / Molecular Weight | C__1__6H__1__7O__5P = 320.28 |
| Physical State (20 deg.C) | Liquid |
| Storage Temperature | Refrigerated (0-10°C) |
| Condition to Avoid | Heat Sensitive |
| CAS RN | 16139-79-0 |
| Reaxys Registry Number | 7218094 |
| PubChem Substance ID | 87568969 |
| MDL Number | MFCD01321165 |
Specifications
| Appearance | Colorless to Yellow to Green clear liquid |
| Purity(GC) | min. 96.0 % |
Properties (reference)
| Boiling Point | 220 °C/3 mmHg |
| Specific Gravity (20/20) | 1.22 |
| Refractive Index | 1.53 |
GHS
Related Laws:
Transport Information:
| H.S.code* | 2931.49-900 |
Application
TCI Practical Example: The Z-Selective Horner-Wadsworth-Emmons Reaction Using Ethyl Diphenyl phosphonoacetate
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Used Chemicals
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Procedure
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Sodium hydride (64 mg, 1.6 mmol, 1.6 eq.) was added to the solution of ethyl diphenylphosphonoacetate (481 mg, 1.5 mmol, 1.5 eq.) in dry THF (5 mL) at -78 °C. The mixture was stirred at same temperature for 30 minutes. Then p-tolualdehyde (120 mg, 1.0 mmol) was added to the reaction mixture at -78 °C and the mixture was stirred 2 hours at same temperature. After that quenched with water (15 mL). The solution was extracted with ethyl acetate (15 mL x 3) and the organic layer was washed with 2 mol/L HCl aq. (10 mL), sat. NaHCO3 aq. (10 mL), and brine (10 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, hexane:ethyl acetate = 20:1) to give 1 as a pale yellow oil (157 mg, 83% yield, E:Z = 1 : 3.67).
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Experimenter’s Comments
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The reaction mixture was monitored by UPLC.
The ratio of E form and Z form was estimated from 1H-NMR.
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Analytical Data
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Compound 1
1H NMR (400 MHz, CDCl3);
1-Z: δ 7.52 (d, J = 8.4 Hz, 2H), 7.16 (d, J = 8.0 Hz, 2H), 6.90 (d, J = 12.8 Hz, 1H), 5.89 (d, J = 12.8 Hz, 1H), 4.19 (q, J = 7.2 Hz, 2H), 2.36 (s, 3H), 1.26 (t, J = 7.2 Hz, 3H).
1-E: δ 7.62 (d, J = 16 Hz, 2H), 7.43 (d, J = 8.0 Hz, 2H), 7.19 (d, J = 8.0 Hz, 1H), 6.40 (d, J = 16.0 Hz, 1H), 4.26 (q, J = 6.8 Hz, 2H), 2.37 (s, 3H), 1.34 (t, J = 6.8 Hz, 3H).
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Lead Reference
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- Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner−Emmons Reagents, Ethyl (Diarylphosphono)acetates
Application
Z-selective Horner－Emmons Reagents
Typical Procedure: A solution of ethyl diphenylphosphonoacetate (0.50 mmol) in THF (10 mL) is treated with Triton B (0.27 mL, 0.60 mmol) at -78 ℃ for 15 min. Benzaldehyde (0.054 mL, 0.53 mmol) is then added, and the resulting mixture is stirred at -78 ℃. The reaction is quenched with saturated NH4Cl, and the mixture is extracted with AcOEt (10 mL×3). The combined extracts are washed with water (15 mL×2) followed by brine, dried (MgSO4) and concentrated. The isomers are separated by flash chromatography.
References
PubMed Literature
Articles/Brochures
TCIMAIL
[TCI Practical Example] The Z-Selective Horner-Wadsworth-Emmons Reaction Using Ethyl Diphenylphosphonoacetate[TCIMAIL No.097] New Z-selective Horner-Emmons Reagents
[Product Highlights] Z-selective Horner－Emmons Reagents
Product Documents (Note: Some products will not have analytical charts available.)
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Specifications
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