Propargyl alcohol → Ethyl 2-(2-propynyloxy)-1,3-thiazole-4-carboxylate

HRID 2261300Notes

Reaction equation

HRID 2261300 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[H-].[Na+].Cl[C:8]1[S:9][CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:4][C:8]1[S:9][CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1)[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13106141Ethyl 2-chlorothiazole-4-carboxylate

Product 1

HCID 57736338Ethyl 2-(2-propynyloxy)-1,3-thiazole-4-carboxylateYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.20 g of propargyl alcohol was dissolved in 20 ml of tetrahydrofuran, and 0.13 g of 60% sodium hydride was added at room temperature. The mixture was stirred at room temperature for 1 hour. After 0.50 g of ethyl 2-chloro-1,3-thiazole-4-carboxylate was added, the reaction 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 0.33 g of ethyl 2-(2-propynyloxy)-1,3-thiazole-4-carboxylate.

Workup

  1. stirringthe reaction 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-43a0b3afc9774a9f938458318588db7d
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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