Ethanol → Ethyl (3R)-4-cyano-3-hydroxybutanoate

HRID 1356576Notes

Reaction equation

[C:1]([CH2:3][C@@H:4]([OH:9])[CH2:5][C:6]([OH:8])=[O:7])#[N:2].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:21](O)[CH3:22]>>[CH2:21]([O:7][C:6](=[O:8])[CH2:5][C@H:4]([OH:9])[CH2:3][C:1]#[N:2])[CH3:22]

Participants

Reactant 4

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 10340Sodium Carbonate

HCID 10236005(R)-4-cyano-3-hydroxybutyric acid

Product 1

HCID 2733879Ethyl (3R)-4-cyano-3-hydroxybutanoateYield 90%

Procedure

(R)-4-cyano-3-hydroxybutyric acid (1.0 mol) in ethanol (500 ml) and conc. sulfuric acid (5 g) were refluxed for 5 hours. The reaction mixture was neutralized with sodium carbonate ancd filtered. The filtrate was concentrated in vacuo to afford (R)-4-cyano-3-hydroxybutyric acid ethyl ester (141 g, 90%).

Workup

filtrationfiltered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-e1fbd4875dcf4b14bb30f0aed73e87cf
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586616B1

Reaction notes

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