Water → Ethyl 3-(3,5-dimethylphenyl)-2-azido-2-propenoate

HRID 844438Notes

Reaction equation

HRID 844438 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH:5]=O.[N:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N+:12]=[N-:13].[O-]CC.[Na+].O>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:14]([N:11]=[N+:12]=[N-:13])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=[C:8]([CH3:10])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 34225Benzaldehyde, 3,5-dimethyl-HCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 86758008Ethyl 3-(3,5-dimethylphenyl)-2-azido-2-propenoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

A mixture of 5 g of 3,5-dimethylbenzaldehyde and 19.3 g of ethyl azidoacetate is added, at −10° C. under dry nitrogen, to a mixture of 25 ml of ethanol and 50 ml of a 21% solution of sodium ethoxide in ethanol. The mixture is left stirring for 1 hour at −10° C. and for fourteen and a half hours at +5° C. It is poured into 100 ml of water and the precipitate formed is filtered off and washed with water. The precipitate is dissolved in ether and this solution is dried over MgSO4 and then evaporated to give the product, which is used without further purification in the subsequent step.

Workup

  1. waitThe mixture is left
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. dissolutionThe precipitate is dissolved in ether
  6. dry with materialthis solution is dried over MgSO4
  7. customevaporated
  8. customto give the product, which
  9. customis used without further purification in the subsequent step

Sources & evidence

ORD record
ord-e5524bdcca9f408da3601d2207e42fd8
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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