Sodium Cyanide → (R)-4-cyano-3-hydroxybutyric acid, n-butyl ester

HRID 1647335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647335
Cl[CH2:2][C@@H:3]([OH:12])[CH2:4][C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6].[C-:13]#[N:14].[Na+]>CS(C)=O>[C:13]([CH2:2][C@@H:3]([OH:12])[CH2:4][C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6])#[N:14]

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 13705504n-butyl (S)-(-)-4-chloro-3-hydroxybutyrate

Produkt 1

HCID 54237719(R)-4-cyano-3-hydroxybutyric acid, n-butyl esterAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The resulting compound was cyanogenated in the same manner as in Example 1-(2). That is, 58.5 g (0.3 mol) of n-butyl (S)-(-)-4-chloro-3-hydroxybutyrate was dissolved in 180 ml of dimethyl sulfoxide, and 67.5 ml of an aqueous solution containing 16.7 g (0.34 mol) of sodium cyanide was added thereto, followed by stirring at 65° C. for 2 hours. The reaction mixture was worked up in the same manner as in Example 1-(2) to obtain n-butyl (R)-(-)-4-cyano-3-hydroxybutyrate in a percent yield of 58%.

Aufarbeitung

  1. additionwas added

Quellen und Nachweise

ORD-Eintrag
ord-1011ff872c5a4ca8b0dd82d6952cd375
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05430171

Notizen zur Reaktion

Wird geladen…