Propargyl alcohol → 2-(2-Propyn-1-yloxy)-5-thiazolecarboxaldehyde

HRID 2261303Notes

Reaction equation

HRID 2261303 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[H-].[Na+].Cl[C:8]1[S:9][C:10]([CH:13]=[O:14])=[CH:11][N:12]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:4][C:8]1[S:9][C:10]([CH:13]=[O:14])=[CH:11][N:12]=1)[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 14797652-Chloro-1,3-thiazole-5-carbaldehyde

Product 1

HCID 577363172-(2-Propyn-1-yloxy)-5-thiazolecarboxaldehydeYield 130.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.37 g of propargyl alcohol was dissolved in 100 ml of tetrahydrofuran, and 0.9 g of 60% sodium hydride was added in portions. The mixture was stirred at room temperature for 1 hour. Thereafter, 3.0 g of 2-chloro-1,3-thiazole-5-carbaldehyde was added to the reaction mixture and the mixture was stirred at room temperature for 3 hours. After aqueous saturated ammonium chloride was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.44 g of 2-(2-propynyloxy)-1,3-thiazole-5-carbaldehyde.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionthe reaction mixture was extracted with methyl-t-butyl ether
  3. washThe organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9925c7cb4206487793944780c0db7ddf
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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