Sulfuric Acid → Ethyl 3-cyano-4,4,5,5,5-pentafluoro-3-hydroxypentanoate

HRID 2387243

Reaktionsgleichung

Reaktionsgleichung von HRID 2387243
[C-:1]#[N:2].[K+].[F:4][C:5]([F:18])([C:14]([F:17])([F:16])[F:15])[C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].S(=O)(=O)(O)O>O.CCO>[C:1]([C:6]([OH:13])([C:5]([F:18])([F:4])[C:14]([F:15])([F:16])[F:17])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2]

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 522203Ethyl 4,4,5,5,5-Pentafluoro-3-oxovalerate

Produkt 1

HCID 86646544Ethyl 3-cyano-4,4,5,5,5-pentafluoro-3-hydroxypentanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of KCN (1.4 eq.) in water (0.5 M) was added with stirring to an ice-cooled solution of ethyl 4,4,5,5,5-pentafluoro-3-oxopentanoate (1 eq.) in EtOH and water (40:60 vol). The mixture was stirred for 6 h at 0° C. and then acidified with 6N sulphuric acid and extracted with Et2O. The organic phase was dried (Na2SO4), and the solvents were removed under reduced pressure. The residue was vacuum distilled. The product fraction was collected at 74-76° C./0.5 mbar. (400 MHz, CDCl3) δ: 5.88 (1H, s), 4.40-4.23 (2H, m), 3.04 (1H, s), 1.33 (3H, t, J=7.1 Hz).

Aufarbeitung

  1. extractionextracted with Et2O
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customthe solvents were removed under reduced pressure
  4. distillationdistilled
  5. customThe product fraction was collected at 74-76° C./0.5 mbar

Quellen und Nachweise

ORD-Eintrag
ord-8896f9ccbbb048a8acabd0b92b467d4a
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268827B2

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