Methanol → HCID 14225608, compound

HRID 1250135Notes

Reaction equation

HRID 1250135 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.[CH3:14]O>C(Cl)Cl>[C:1]([O:4][C@@:12]([CH3:14])([CH2:11][CH2:10][CH3:9])[C:13]#[N:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic Anhydride

Product 1

HCID 14225608HCID 14225608, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The purified cyanohydrin was dissolved in 2 ml of absolute methylene chloride and the solution was treated at room temperature with 2 mol equivalents of acetic anhydride and with 2 mol equivalents of pyridine and stirred at room temperature for 34 hours with exclusion of moisture. 350 μl of absolute methanol were then added and the mixture was stirred at room temperature for 0.5 hour. It was then diluted with 10 ml of methylene chloride and extracted with 10 ml each of 5% H2SO4, distilled water and saturated NaHCO3 solution and dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. 112 mg (95%) of (S)-2-acetoxy-2-methylpentanenitrile were obtained. e.e.=75% (determined by gas chromatography)

Workup

  1. stirringthe mixture was stirred at room temperature for 0.5 hour
  2. extractionextracted with 10 ml each of 5% H2SO4
  3. distillationdistilled water and saturated NaHCO3 solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-041517af22b74eb8bd70d6075fc67378
Source dataset
uspto-grants-2002_01
Patent number
US06337196B1

Reaction notes

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