Trifluoro ethanone

N.B. The l-[5-Chloro-2-hydroxy-4-(octadecanoyloxy)phenyl]-2,2,2-trifluoro-ethanone (II) is the most likely formnla. 

Reaction of the thia-amino acid 392 with trifluoroacetic anhydride gave the 2,2,2-trifluoro-l-[7-(trifluoromethyl)-l//-pyrrolo[l,2-c]-[l,3]thiazol-6-yl] ethanone pyrrole 395. The formation of the pyrrole can be rationalized by a sequence involving trifluoroacetylation of the enamine 392 affording dione 393 followed by loss of water and carbon dioxide to give the aromatic product 395. These decarboxylations afford fluorinated derivatives of heterocyclic skeletons known to exhibit interesting biological activity (Scheme 58) <2000T7267>. 

The synthesis reported by Nassal is based on the Ca-alkylation of diethyl 2-(ace-tylamino)malonate by 3-[4-(bromomethyl)phenyl]-3-(trifluoromethyl)-3//-diazirine (46) (Scheme 12) J122l The precursor for the diazirine-containing alkylating agent is 2,2,2-trifluoro-l-(4-tolyl)ethanone (39).1124 ... 

Therapeutic Function Acetylcholinesterase inhibitor Chemical Name Ethanone, 2,2,2-trifluoro-l-(3-(trimethylsilyl)phenyl)-Common Name Zifrosilone Structural Formula ... 

Trifluoro-l-phenyl-ethanone (25 g) was dissolved in ethyl alcohol at 80 °C and hydroxylamine oxime (0.151 mol) and sodium acetate (0.245 mol) dissolved in 20 ml water added. The mixture refluxed overnight and was then concentrated. The residue was poured into water and a white precipitate isolated and directly in Step 2. 

Trifluoro-l-phenyl-ethanone-oxime-O-(10-camphoryl-sulfonate)... 

Demir, A. S., Sesenoglu, O. and Gercek-Arkin, Z. (2001) An asymmetric synthesis of both enantiomers of 2,2,2-trifluoro-l-furan-2-yl-ethylamine and 3,3,3-trifluoroalanine from 2,2,2-trifluoro-l-furan-2-yl-ethanone. Tetrahedron Asymmetry, 12, 2309-2313. 

The acetone powder of G. candidum (APG4) has also been used for the reduction of sulfur containing trifluoromethyl ketones (Fig. 15-34) 183l This reaction can be scaled up easily without the loss of enantioselectivity. For example, the reduction of trifluoro(2-thienyl)ethanone on the gram scale proceeded quantitatively and yielded the optically pure (R)-alcohol in 88% yield after purification (4.16 g, ee > 99%). The thienyl alcohol can be further transformed into a fluorinated aliphatic alcohol without racemization. 

The Perkin reaction has been used to synthesize trifluoromethyl-containing building blocks that are very useful in the pharmaceutical and agrochemical industries. For example, 2,2,2-trifluoro-l-(4-methylphenyl)ethanone (43) reacts with acetic anhydride, when heated in the presence of sodium acetate, to produce 3-polyfluoroalkyl- -cinnamic acid 44.11... 

A series of l-aryl-3,3,3-trifluoro-I-ethanones 77 have been synthesized from the reaction of F02SCF2CC>2Me with p-bromoenol phosphate 76 in the presence of Cul in moderate yields. Enol phosphates are versatile intermediates in organic synthesis.17... 

Interestingly, other benzyne sources accomphsh the same end. Thus, as shown in Scheme 10.27, when the orf/jo-trifluoromethanesulfonate (triflate,-OTf) derivative of phenyltrimethylsilane [i.e., 2-(trimethyIsilyl)-phenyl triflate] is treated with cesium fluoride in acetonitrile (cyanomethane) at room temperature in the presence of iV-phenyltrifluoroacetamide, 2,2,2-trifluoro-l-[2-(phenylamino)phenyl]ethanone results. Presumably, elimination occurs to produce benzyne, and this is followed by addition and rearrangement. 

Ci7H2,F30 2, 2-trifluoro-l-[4-(4-propyl-cyclohexyl)- phenyl]-ethanone 121040-03-7... 

C19H25F3O 2,2,2-trifluoro-l-[4-(4-pentyl-cyclohexyl)-phenyl] -ethanone 136101-34-3... 

Preparation by reaction of hydroxylamine hydrochloride with 2,2,2-trifluoro-l-(3-methoxy-phenyl)ethanone in refluxing methanol for 2 h (97%) [6124]. 

Trifluoro-l-(2-hydroxy-5-methyl-3-nitrophenyl)ethanone, 1270 C,H/3N03... 

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