Diethyl perfluoroglutarate → HCID 20561439, compound

HRID 1155597Notes

Reaction equation

HRID 1155597 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[F:13][C:14]([F:31])([C:20]([F:30])([F:29])[C:21]([F:28])([F:27])[C:22]([O:24][CH2:25][CH3:26])=O)[C:15]([O:17]CC)=[O:16]>O1CCCC1>[CH2:25]([O:24][CH:22]1[C:21]([F:27])([F:28])[C:20]([F:29])([F:30])[C:14]([F:13])([F:31])[CH:15]([OH:16])[O:17]1)[CH3:26]

Participants

4

Reactant 2

HCID 9874Diethyl perfluoroglutarateHCID 16684438Red-Al2×

Product 1

HCID 20561439HCID 20561439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

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).

Workup

  1. customat -70° C
  2. customto give 16.8 g

Sources & evidence

ORD record
ord-231e2a0ceaba47e4b36cad08fda0b796
Source dataset
uspto-grants-1981_11
Patent number
US04302612

Reaction notes

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