Potassium Hydroxide → HCID 57455069, compound

Participants

Reaction Conditions

Reaction Steps

Referring to scheme (17A) above, to a three-neck 500 mL flask equipped with a agitator, an inlet for a starting material addition, and a packed column topped with a reflux distillation head, thermocouple, and collection flask can be charged 60.40 g of KOH (0.917 mole), 5.86 g of Methyltributylammonium chloride (Aliquat 175, ˜5% by wt) in 150 mL of deionized water to form a solution. The resulting solution can be heated 97° C. and 110 g (0.281 mole) 1,1,1,2,5,5,5-heptafluoro-2-(trifluoromethyl)-4-iodopentane can be added drop-wise and sub-surface via syringe pump over the course of 2 hr period. During this addition the resulting product can be collected in the overhead collection flask and the reaction can be continued to be heated until the overhead temperature reached 94° C. The collected material can be dried over magnesium sulfate to give 74.18 g of crude reaction product which by GC analysis consisted on primary product and starting material. The crude reaction material was distilled to afford 42.6 g of (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene (57.5% isolated yield). (1H-NMR (CDCl3): □ 6.45 (d, J=12 Hz, 1H), 6.45 (dhep, 1H). 13C-NMR (CDCl3): 90.5 (dhep, J=27, 202 Hz, CFCH), 120 (qd, 27, 287 Hz, CF3CF), 121.6 (q, J=220 Hz, CHCF3), 124.4 (m, CHCF), 128.2 (qd, J=21, 36 Hz, CHCF3). 19F-NMR (CDCl3w/CCl3F): □ −66.4 (d, JH−F=3 HzCF3CH), −76.9 (d, JF−F=8 Hz, CF3CF), −186.9 (m, CF3CF).

Provenance & Evidence