Cyanoacetic acid → 3-(2-Cyano-acetoxy)-butyric acid ethyl ester

HRID 1294048Notes

Reaction equation

HRID 1294048 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH:6]([OH:8])[CH3:7])[CH3:2].[C:10]([CH2:12][C:13](O)=[O:14])#[N:11].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH:6]([O:8][C:13](=[O:14])[CH2:12][C:10]#[N:11])[CH3:7])[CH3:2]

Participants

6

Reactant 3

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 62572Ethyl 3-Hydroxybutyrate

Product 1

HCID 866079533-(2-Cyano-acetoxy)-butyric acid ethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 194.0 g of ethyl-3-hydroxybutyrate, 149.83 g of cyanoacetic acid, and 10.76 g of 4-dimethylaminopyridine (DMAP) was stirred in 1500 ml of CH2Cl2 in a 3 L three-neck round bottom flask equipped with a mechanical stirrer. About 75 ml of N-N′-dimethylformamide (DMF) was added to the above mixture to make a clear solution. The above solution was chilled in an ice water bath. A separately prepared dicyclohexylcarbodiimide (DCC) solution (363.45 g in 600 ml CH2Cl2) was added to the above chilled solution by using an addition funnel. White precipitate formed within five minutes after the start of the addition. The reaction mixture was left stirred overnight.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe above solution was chilled in an ice water bath
  3. customWhite precipitate formed within five minutes
  4. additionafter the start of the addition
  5. waitThe reaction mixture was left

Sources & evidence

ORD record
ord-a173ea4e1b0a4512a5bf97dc3feb29d9
Source dataset
uspto-grants-2007_07
Patent number
US07238828B2

Reaction notes

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