Sodium Azide → 5-(3-(2-Azidoethyl)benzyl)-3-isobutoxycyclopent-2-enone

HRID 41142Notes

Reaction equation

HRID 41142 reaction equation
I[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][CH:8]1[C:12](=[O:13])[CH:11]=[C:10]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:9]1.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C)C=O.O>[N:22]([CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][CH:8]1[C:12](=[O:13])[CH:11]=[C:10]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:9]1)=[N+:23]=[N-:24]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 547576605-(3-(2-Iodoethyl)benzyl)-3-isobutoxycyclopent-2-enone

Product 1

HCID 547576615-(3-(2-Azidoethyl)benzyl)-3-isobutoxycyclopent-2-enoneYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 30 (0.044 g, 0.11 mmol) and sodium azide (0.007 g, 0.11 mmol) in dry N,N-dimethylformamide (0.5 mL) was heated to 50° C. for 45 minutes. The reaction mixture was diluted with water and the resulting mixture extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue so obtained was dried under high vacuum to furnish the desired compound. Yield: 76%.

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue so obtained
  7. customwas dried under high vacuum

Sources & evidence

ORD record
ord-c427f81bc92d4f75aa74c67d803300f3
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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