Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester
![Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester Structure](CAS/20180601/GIF/88738-84-5.gif)
- CAS No.
- 88738-84-5
- Chemical Name:
- Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester
- Synonyms
- Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester
- CBNumber:
- CB83280447
- Molecular Formula:
- C8H11F6O5P
- Molecular Weight:
- 332.13
- MOL File:
- 88738-84-5.mol
- Modify Date:
- 2023/7/12 17:09:11
| Boiling point | 260.0±40.0 °C(Predicted) |
|---|---|
| Density | 1.418±0.06 g/cm3(Predicted) |
| solubility | Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly) |
| form | Oil |
| color | Colourless to Pale Yellow |
| Stability | Moisture Sensitive |
Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester Chemical Properties,Uses,Production
Uses
Methyl 2-[Bis(2,2,2-trifluoroethoxy)phosphinyl]propionate is synthetic reagent used in Z-selective HWE reactions (a.k.a. Still-Genari modification) to make alpha,β-unsaturated esters. Methyl 2-[Bis(2,2,2-trifluoroethoxy)phosphinyl]propionate is used as reagent/reactant for preparation of (±)-(Z)-2β-hydroxy-14-hydro-β-santalol via tandem radical cyclization.
Synthesis
KHMDS (8.0 mL, 4.00 mmol, 0.5M in toluene) was added by syringe to a solution of dried 18-crown-6 (4.20 g, 15.89 mmol), THF (20 mL), and Bis (2,2,2-trifluoroethyl) phosphite (0.55 mL, 3.75 mmol) at -78 ℃. Following 15 min, methyl 2-bromopropionate (0.35 mL, 3.14 mmol) was added to the reaction flask. The reaction mixture was allowed to warm to room temperature for 4hr. The standard workup protocol was followed, then the crude product was purified by flash column chromatography (9:1-3:2 hexanes:EtOAc, Rf = 0.22 in 1:1 hexanes:EtOAc) yielding Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester (103 mg, 31 mmol, 9.9%) as a yellow syrup.