Ethyl Acetate → HCID 123961406, compound

HRID 1050205Notes

Reaction equation

HRID 1050205 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C@H:6]([OH:10])[CH2:7][C:8]#[N:9])[CH3:2].[CH3:12]C(=O)OCC>IC.[Ag]=O>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH:6]([O:10][CH3:12])[CH2:7][C:8]#[N:9])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl Acetate2×HCID 2733879Ethyl (3R)-4-cyano-3-hydroxybutanoate

Product 1

HCID 123961406HCID 123961406, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6328Methyl iodideSolvent

Procedure

(R)4-cyano-3-hydroxy butyric acid ethyl ester (1.5 g, 9.54 mmol) was dissolved in iodomethane (20 ml). Silver oxide solid (3.3 g, 14.32 mmol) was added, and the reaction mixture was agitated at room temperature overnight. TLC (PE/EA=2/1) was employed to monitor the reaction. After the reaction completed, the silver oxide solid was removed by filtration, and the solvent was evaporated. Column chromatography (PE/EA=10/1) afforded colorless transparent liquid 1.0 g, yield 63.1%.

Workup

  1. customthe reaction
  2. customthe silver oxide solid was removed by filtration
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-182fc92041184b01b0ff21b86fbc8f72
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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