Acetic Anhydride → HCID 18433854, compound

HRID 2305939Notes

Reaction equation

HRID 2305939 reaction equation
[CH:1]1([CH2:6][CH2:7][CH:8]([CH3:13])[CH2:9][CH:10]=[N:11]O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC(=O)C)(=O)C>>[CH:1]1([CH2:6][CH2:7][CH:8]([CH3:13])[CH2:9][C:10]#[N:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 73444834HCID 73444834, compound

Product 1

HCID 18433854HCID 18433854, compoundYield 57.5%

Procedure

5-cyclopentyl-3-methylpentanal oxime (3.7 g; 20 mmol) and acetic anhydride (4.5 g; 40 mmol) were heated at 110° C. during 1.5 hours, poured into ice-water (100 ml), and extracted with MTBE (150 ml). The organic phase was washed with brine (4×150 ml), dried (MgSO4), concentrated in, vacuo, and purified by flash chromatography (MTBE/hexane 1:15) to give 1.9 g (57% yield) of 5-cyclopentyl-3-methylpentanenitrile.

Workup

  1. extractionextracted with MTBE (150 ml)
  2. washThe organic phase was washed with brine (4×150 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in, vacuo
  5. custompurified by flash chromatography (MTBE/hexane 1:15)

Sources & evidence

ORD record
ord-5a9213e1b4a147279e7c40985811aaed
Source dataset
uspto-grants-2002_08
Patent number
US06441052B1

Reaction notes

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