2-Methylpentaldehyde → 2-Azidocarbonylpentane
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
Product 1
Reagents, catalysts & solvents 1
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
- stirringThe mixture was stirred another 5 hours
- filtrationfiltered through silica gel
- 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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