Ethyl Acetate → 2-Methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carbaldehyde

HRID 972237Notes

Reaction equation

HRID 972237 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH2:17][OH:18])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:6]=1.C(OCC)(=O)C.CCCCCCC>ClCCl>[CH3:1][C:2]1[S:3][C:4]([CH:17]=[O:18])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 214064172-Methyl-4-(6-carbomethoxyhexyl)-5-hydroxymethyl-thiazole

Product 1

HCID 214064152-Methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carbaldehydeYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of 2.8 g of crude 2-methyl-4-(6-carbomethoxyhexyl)-5-hydroxymethyl thiazole (XII, R1 = CH3) in 25 ml of dichloromethane was dropwise added to the solution of 16 g of chromium trioxide-dipyiridine complex in 320 ml of dichloromethane. Stirring of the reaction mixture was continued for 30 minutes, then the reaction mixture was filtered and the filtrate was evaporated in vacuo. After purifying the crude product obtained as evaporation residue, by preparative thin layer chromatography using a silica gel layer as adsorbent and a mixture of 50 % ethyl acetate and 50 % of n-heptane as running solvent, 2.15 g of 2-methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carbaldehyde (XIII, R1 = CH3) were obtained.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customAfter purifying the crude product
  4. customobtained as evaporation residue, by preparative thin layer chromatography

Sources & evidence

ORD record
ord-fd308d2c45654f12bcfe52db554f5dc1
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

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