2-Thiophenecarboxaldehyde → Ethyl 2-azido-3-(2-thienyl)propenoate

HRID 1017728Notes

Reaction equation

HRID 1017728 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=O.[O-]CC.[K+].[Cl-].[NH4+]>C(O)C>[N:1]([C:4](=[CH:15][C:11]1[S:10][CH:14]=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 23670592Potassium ethoxide

Product 1

HCID 54362140Ethyl 2-azido-3-(2-thienyl)propenoateYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl azidoacetate (1.38 g) and thiophene-2-carboxaldehyde (1 g) in ethanol (20 ml) was added dropwise to a solution of potassium ethoxide (0.9 g) in ethanol (20 ml) at 0° C. The reaction was stirred for 2 hours at 0° C. and 2 hours at ambient temperature then poured into saturated aqueous ammonium chloride solution (150 ml) and extracted with ether. Combined organic extracts were dried (MgSO4), concentrated in vacuo and the residue purified by column chromatography using isohexane as eluent to give the product as a pale yellow crystalline solid (0.49 g, 25%), NMR d(CDCl3) 1.40 (3H, t), 4.37 (2H, q), 7.08 (2H, m), 7.18 (1H, s), 7.38 (1H, m), 7.52 (1H, d).

Workup

  1. extractionextracted with ether
  2. dry with materialCombined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-080d2bc859cf421d8a886680a13be622
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

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