Ethyl (hexyl) 2,2-difluoro-2-(trimethylsilyl)ethyl acetate

Ethyl 2,2-Difluoro-2-(trimethylsilyl)acetate [205865-67-4] C7H14F2O2Si (MW 196.27) InChI = 1S/C7H14F2O2Si/c1-5-11-6(10)7(8,9)12(2,3)4/h5H2,1-4H3 InChIKey = DYAKYYSMROBYNG-UHFFFAOYSA-N Hexyl 2,2-Difluoro-2-(trimethylsilyl)acetate [225235-58-5] C11H22F2O2Si (MW 252.37) InChI = 1S/C11H22F2O2Si/c1-5-6-7-8-9-15-10(14)11(12,13)16(2,3)4/h5-9H2,1-4H3 InChIKey = UUNGLZFJKUWKPT-UHFFFAOYSA-N (versatile building blocks for introduction of CF2CO2R groups) Physical Data: R = Et, bp 70–72 °C/25 mmHg1; bp 55 °C/20 mmHg2; bp 100 °C/32 mmHg3; bp 110 °C/91 mmHg.4 R = hexyl, bp 80 °C/2 mmHg.5 Solubility: soluble in most organic solvents. Form Supplied in: colorless liquid; commercially available. Analysis of Reagent Purity: 1H, 13C, and 19F NMR. Handling, Storage, and Precautions: is base-sensitive and generally stable if stored in tightly closed containers under cool, dry conditions with adequate ventilation. Preparative Methods: prepared by the deprotonation/silylation of ethyl difluoroacetate1; by Reformatsky-type reactions (electrochemical reduction2, 5, 6 or low-valent metal-mediated reduction)3, 4, 7 (eq 1). (1) Among them, Mg-promoted defluorinative silylation of ethyl trifluoroacetate (eq 2) and dechlorinative silylation of ethyl chlorodifluoroacetate (eq 3) are convenient methods to prepare ethyl 2,2-difluoro-2-(trimethylsilyl)acetate in good yield.3, 4 (2) (3)