Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester synthesis

5synthesis methods

Product Name:Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester
CAS Number:88738-84-5
Molecular formula:C8H11F6O5P
Molecular Weight:332.13

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.

88738-78-7 Synthesis

BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE

88738-78-7
118 suppliers
$45.00/1g

74-88-4
343 suppliers
$15.00/10g

Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester

88738-84-5
3 suppliers
inquiry

Yield:88738-84-5 91%

Reaction Conditions:

Stage #1: bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonatewith potassium tert-butylate in tetrahydrofuran at 0; for 0.5 h;Inert atmosphere;
Stage #2: methyl iodide in tetrahydrofuran at 0 - 20; for 24 h;Inert atmosphere;

References:

Tu, Qian;Wang, Zheyuan;Zhang, Zhongchao;Huang, Jun;Yang, Zhen [Organic Letters,2021,vol. 23,# 11,p. 4088 - 4093] Location in patent:supporting information