1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 5-(1-azidoethyl)thiophene-2-carboxylate

HRID 1909848Notes

Reaction equation

HRID 1909848 reaction equation
O[CH:2]([C:4]1[S:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=1)[CH3:3].C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:28]([CH:2]([C:4]1[S:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=1)[CH3:3])=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 59355961Ethyl 5-(1-hydroxyethyl)thiophene-2-carboxylate

Product 1

HCID 58306713Ethyl 5-(1-azidoethyl)thiophene-2-carboxylateYield 90.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of ethyl 5-(1-hydroxyethyl)thiophene-2-carboxylate (1.01 g), diphenylphosphorylazide (1.67 g), and toluene (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (905 μL) under ice-cooling, followed by stirring for 30 minutes. The reaction mixture was warmed to room temperature, followed by stirring for 15 hours. The reaction liquid was washed with water and 1 M hydrochloric acid in this order, and dried over anhydrous sodium sulfate. Then, after concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain ethyl 5-(1-azidoethyl)thiophene-2-carboxylate (1.03 g) as a colorless oily substance.

Workup

  1. temperaturecooling
  2. stirringby stirring for 15 hours
  3. customThe reaction liquid
  4. washwas washed with water and 1 M hydrochloric acid in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThen, after concentration under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9544ac1f4e64428db0630cf4b0de3529
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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