Dimethylformamide → 3-(2-Cyano-acetoxy)-hexanoic acid ethyl ester

HRID 1294049Notes

Reaction equation

HRID 1294049 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH:6]([OH:10])[CH2:7][CH2:8][CH3:9])[CH3:2].[C:12]([CH2:14][C:15](O)=[O:16])#[N:13].CN(C=O)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH:6]([O:10][C:15](=[O:16])[CH2:14][C:12]#[N:13])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 61293Ethyl 3-hydroxyhexanoate

Product 1

HCID 248848973-(2-Cyano-acetoxy)-hexanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 100.14 g of ethyl-3-hydroxyhexanoate, 63.75 g of cyanoacetic acid, and 4.58 g of 4-dimethylaminopyridine (DMAP) in 625 ml of CH2Cl2 was stirred in a 2 L three-neck round bottom flask equipped with a mechanical stirrer. About 31 ml of N-N′-dimethylformide (DMF) was added to make a clear solution. The above clear solution was chilled in an ice water bath. A separately prepared dicyclohexylcarbodiimide (DCC) solution (154.75 g in 250 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 clear 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
  6. stirringstirred overnight

Sources & evidence

ORD record
ord-a2de67f5aab143d2abdaf156b65b3994
Source dataset
uspto-grants-2007_07
Patent number
US07238828B2

Reaction notes

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