107905-52-2

Usage

Chemical Properties

Colourless Liquid

Synthesis

KHMDS (7.50 mL, 3.75 mmol, 0.5 M in toluene) was added to a solution of 18- crown-6 (4.10 g, 15.51 mmol), THF (20 mL), and bis (2,2,2-trifluoroethyl) phosphite (1) (0.50 mL, 3.41 mmol) by syringe in a dropwise manner at -78 ℃. Following 15 min, ethyl 2-bromopropionate (0.40 mL, 3.08 mmol) was added to the round bottom flask and the reaction mixture was allowed to stir for 4 hr at room temperature. Following the standard workup procedure, the crude product was then purified by flash column chromatography (3:1 to 2:1 hexanes:EtOAc, Rf = 0.33 in 1:1 hexanes:EtOAc) yielding Ethyl 2-[Bis(2,2,2-trifluoroethyl)phosphono] Propionate (112 mg, 0.33 mmol, 10.5%) as a yellow syrup.

InChI:InChI=1/C9H13F6O5P/c1-3-18-7(16)6(2)21(17,19-4-8(10,11)12)20-5-9(13,14)15/h6H,3-5H2,1-2H3

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 107905-58-8 1-ethoxycarbonylethylphosphonyl dichloride 
• 92466-70-1 bis(2,2,2-trifluoroethyl)phosphite 
• 535-11-5 Ethyl 2-bromopropionate 
• 370-69-4 tris(2,2,2-trifluoroethyl)phosphite 
• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 107905-57-7 bis-(trimethylsilyl)-2-carboethoxyethylphosphonate 
• 650-16-8 ethylphosphonic acid bis-(2,2,2-trifluoroethyl) ester 

Downstream Products

• 101376-73-2 Methyl (E)-4-(benzyloxy)-2-methyl-2-butenoate 
• 101020-38-6 (Z)-ethyl 4-(benzyloxy)-2-methyl-2-butenoate 
• 138152-64-4 (Z)-5-Benzyloxy-2-methyl-pent-2-enoic acid ethyl ester 
• 112890-05-8 (Z)-4-(2-Benzyloxy-4,6-dimethoxy-phenyl)-2-methyl-but-2-enoic acid ethyl ester 
• 74974-72-4 ethyl (4S)-(Z)-4-(N-benzyl-p-toluenesulfonamido)-2-methyl-5-phenylpent-2-enoate 
• 74974-73-5 ethyl (4S)-(E)-4-(N-benzyl-p-toluenesulfonamido)-2-methyl-5-phenylpent-2-enoate 
• 118574-90-6 (Z)-3-((2S,3S)-3-Benzyloxymethyl-2-methyl-oxiranyl)-acrylic acid ethyl ester 
• 143812-50-4 (Z)-(S)-5-(2-Benzyloxy-ethyl)-2-methyl-hepta-2,6-dienoic acid ethyl ester 
• 153628-72-9 (Z)-(4R,5S,6R)-7-Benzyloxy-2,4,6-trimethyl-5-triisopropylsilanyloxy-hept-2-enoic acid ethyl ester 
• 185909-48-2 (Z)-(5S,7S)-8-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-oct-2-enoic acid ethyl ester 
• 201670-53-3 (2Z,6Z)-8-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienoic acid ethyl ester 
• 201004-59-3 (Z)-4-[3,4-Dimethyl-5-(tetrahydro-pyran-2-yloxy)-2-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-2-methyl-but-2-enoic acid ethyl ester 
• 198768-52-4 ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate 
• 380414-33-5 (Z)-4-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-2-methyl-but-2-enoic acid 

Relevant academic research and scientific papers

A new bis(2,2,2-trifluoroethyl)phosphonate for the synthesis of Z-unsaturated N-methoxy-N-methylamides

The N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide was easily obtained via the Arbuzov reaction with use of commercially available tris(2,2,2-trifluoroethyl)phosphite, 2-bromo-N-methoxy-N-methylacetamide, and KF/alumina. The reaction of bis(2,2,2-trifluoroethyl)phosphonate with several aldehydes demonstrates the versatility of the method, which gives Z-unsaturated amides in good yields.

A convenient method for the synthesis of bis-trifluoroethyl phosphonoacetates

Bis-trifluoroethyl phosphonoacetates were easily obtained by condensation of bis-trifluoroethyl alkylphosphonates with alkyl chloroformates in the presence of 2 equivalents of lithium hexamethyldisilazane (LiHMDS).

A HIGHLY SELECTIVE SYNTHESIS OF A CHIRAL GAMMA-AMINO TRISUBSTITUTED Z-VINYL ESTER.

Application of the Clark Still trifluoroethyl phosphonate varient of the Wadsworth-Emmons reaction with a chiral alpha-amino aldehyde results in the highly selective synthesis of a trisubstituted Z-vinyl ester.