Azobisisobutyronitrile → Octanal

HRID 851413Notes

Reaction equation

HRID 851413 reaction equation
CC1(C)O[CH2:8][CH2:7][C@H:6]2N1[C:4](=[O:12])[C@@H:5]2[N+]#[C-].N(C(C)(C)C#N)=N[C:16](C)([CH3:19])[C:17]#N>C1C=CC=CC=1>[CH3:17][CH2:16][CH2:19][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[O:12]

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 54269083(6R,7R)-2,2-dimethyl-7-isocyano-1-aza-3-oxabicyclo[4.2.0]octan-8-one

Product 1

HCID 454OctanalYield 896.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (6R,7R)-2,2-dimethyl-7-isocyano-1-aza-3-oxabicyclo[4.2.0]octan-8-one (150 mg), tribulyltinhydride (0.263 ml), and azobisisobutyronitrile (14 mg) in benzene (4.5 ml) was refluxed for 15 minutes. The resulting solution was chromatographed on silica gel (4.5 g) eluting with a mixture of benzene and acetone (15:1-6:1) to give the crude product (140 mg) as an oil, which was purified by silica gel (5 g) chromatography (eluate: a mixture of methylene chloride and ethyl acetate 30:1-5:1) to give (6R)-2,2-dimethyl-1-aza-3-oxabicycle[4.2.0]octan-8-one (98 mg) as an oil.

Workup

  1. temperaturewas refluxed for 15 minutes
  2. customThe resulting solution was chromatographed on silica gel (4.5 g)
  3. washeluting with a mixture of benzene and acetone (15:1-6:1)
  4. customto give the crude product (140 mg) as an oil, which
  5. customwas purified by silica gel (5 g) chromatography (eluate
  6. additiona mixture of methylene chloride and ethyl acetate 30:1-5:1)

Sources & evidence

ORD record
ord-de34bde2077b4c589dc097cb1289293c
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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