Sodium Chloride → [2-(2-Propynyloxy)-thiazol-4-yl]methanol

HRID 2261301Notes

Reaction equation

HRID 2261301 reaction equation
[CH2:1]([O:4][C:5]1[S:6][CH:7]=[C:8]([C:10](OCC)=[O:11])[N:9]=1)[C:2]#[CH:3].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][OH:11])[N:9]=1)[C:2]#[CH:3]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 57736338Ethyl 2-(2-propynyloxy)-1,3-thiazole-4-carboxylate

Product 1

HCID 57736290[2-(2-Propynyloxy)-thiazol-4-yl]methanolYield 91.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a nitrogen atmosphere, 0.30 g of ethyl 2-(2-propynyloxy)-1,3-thiazole-4-carboxylate was dissolved in 10 ml of tetrahydrofuran, and 3.3 ml of a solution (1 mol/L) of diisobutylaluminum hydride in toluene was added dropwise at 0° C. The mixture was stirred at 0° C. for 1 hour. The reaction mixture was added to aqueous saturated sodium chloride and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 0.22 g of [2-(2-propynyloxy)-thiazol-4-yl]methanol.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c5bc818bbee4e0197c53e7480a499d0
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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