Methyl 2-azidoacetate → 2-Azido-3-(4-bromo-5-methyl-thiophen-2-yl)-acrylic acid methyl ester

HRID 1951638Notes

Reaction equation

HRID 1951638 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][N:5]=[N+:6]=[N-:7].[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=O)[S:13][C:14]=1[CH3:15].C[O-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:8])[C:4]([N:5]=[N+:6]=[N-:7])=[CH:16][C:12]1[S:13][C:14]([CH3:15])=[C:10]([Br:9])[CH:11]=1

Participants

5

Reactant 3

HCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium MethoxideHCID 155382124-Bromo-5-methylthiophene-2-carbaldehyde

Product 1

HCID 767450662-Azido-3-(4-bromo-5-methyl-thiophen-2-yl)-acrylic acid methyl esterYield 81.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of azido-acetic acid methyl ester (25 g, 220 mmol) and 4-bromo-5-methyl-thiophene-2-carbaldehyde (15 g, 73 mmol) in 50 ml of MeOH cooled at −25° C. was added a solution NaOMe in MeOH (51 ml, 4.36 M). The resulting mixture (slush) was stirred with a mechanical stirrer for 2 h at 0° C. and the 200 g of ice was added. The yellow solid was collected by filtration and air-dried to give 18 g of the title product which was used for the next step without further purification.

Workup

  1. filtrationThe yellow solid was collected by filtration
  2. customair-dried

Sources & evidence

ORD record
ord-911601a7ec7648e4bfee224b19ff85a6
Source dataset
uspto-grants-2013_03
Patent number
US08404736B2

Reaction notes

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