Pyridine → HCID 10352102, compound

HRID 1250134Notes

Reaction equation

HRID 1250134 reaction equation
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:14](OCC)[CH3:15]>>[C:1]([O:4][C@@H:12]([CH2:11][CH2:10][CH2:9][CH2:14][CH3:15])[C:13]#[N:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7918Acetic Anhydride

Product 1

HCID 10352102HCID 10352102, compound

Procedure

The purified cyanohydrin was dissolved in 5 ml of dry diethyl ether, and the solution was treated with 2 mol equivalents of acetic anhydride and 2 mol equivalents of pyridine and stirred at room temperature for 8 hours. It was then extracted with 10 ml each of 5% H2SO4, distilled water and saturated NaHCO3 solution, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. After purification by column chromatography, 182 mg of (S)-2-acetoxyheptanenitrile were obtained (98% isolated yield). e.e.=96% (determined by gas chromatography)

Workup

  1. extractionIt was then extracted with 10 ml each of 5% H2SO4
  2. distillationdistilled water and saturated NaHCO3 solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customAfter purification by column chromatography

Sources & evidence

ORD record
ord-074bd3c1248640a787bb34d0a653a4bd
Source dataset
uspto-grants-2002_01
Patent number
US06337196B1

Reaction notes

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