2-Methylpentaldehyde → 2-Azidocarbonylpentane

HRID 1884902Notes

Reaction equation

HRID 1884902 reaction equation
[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].[CH3:8][CH:9]([CH2:12][CH2:13][CH3:14])[CH:10]=[O:11]>ClCCl>[N:1]([C:10]([CH:9]([CH2:12][CH2:13][CH3:14])[CH3:8])=[O:11])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 312452-MethylpentaldehydeHCID 78378Azidotrimethylsilane

Product 1

HCID 235049582-Azidocarbonylpentane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under Ar, a mixture of azidotrimethylsilane (1.15 g, 9.98 mmol) and chromic anhydride (998 mg, 9.98 mmol) was stirred at room temperature till homogeneous solution. The solution of 2-methylpentanal (500 mg, 4.99 mmol) in 5 mL of dichloromethane was added. The mixture was stirred another 5 hours, and then filtered through silica gel. The filtrate was concentrated to give the crude material. FT-IR 2135.80 cm−1, 2110.9 cm−1.

Workup

  1. stirringThe mixture was stirred another 5 hours
  2. filtrationfiltered through silica gel
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-82d3e3bba5cc46fa9742ae1783524b7b
Source dataset
uspto-grants-2004_07
Patent number
US06767922B2

Reaction notes

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