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

HRID 1647335Notes

Reaction equation

HRID 1647335 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

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%.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-1011ff872c5a4ca8b0dd82d6952cd375
Source dataset
uspto-grants-1995_07
Patent number
US05430171

Reaction notes

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