Diethyl hexafluoroglutarate → HCID 20561439, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 30.3 g. (0.015 mol.) of Vitride (70% in benzene) in 30 ml. of dry tetrahydrofuran (THF) was added dropwise over 45 min. to a stirred solution of 25.0 g. (0.084 mol.) of diethyl perfluoroglutarate in 200 ml. of THF at -70° C. The mixture was stirred for an additional 2 hours at -70° C. followed by decomposing the Vitride as described in Example 1 to give 16.8 g. (87% by weight) of the title compound as a pale yellow liquid. Distillation afforded a colorless oil: boiling range 65°-70° C. (1.7 mm); nD26 1.3671; νmaxneat 3350 (broad) cm-1 ; nmr (CDCl3) δ 1.20 (t,3H,J=6.5 Hz), 3.46-4.10 (m,2H,J=4 Hz) 5.07-5.26 (m,2H), 8.33 (bd s, 1H, exch.) which on prolonged storage (1 month) solidified to a white crystalline product; melting range 84°-6° C. (C6H6).

Provenance & Evidence