1-Butanol → 2-Butoxy-1,3-thiazole

HRID 440330Notes

Reaction equation

HRID 440330 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][CH3:6].[H][H].Br[C:11]1[S:12][CH:13]=[CH:14][N:15]=1>CN(C=O)C>[CH2:3]([O:7][C:11]1[S:12][CH:13]=[CH:14][N:15]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 24758Sodium hydrideHCID 764302-BromothiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 224069472-Butoxy-1,3-thiazoleYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of NaH (6.7 mmol, 0.27 g, 60% dispersion) in dry DMF was stirred with butanol (6.09 mmol, 0.55 mL) under argon until evolution of hydrogen ceased. 2-Bromothiazole (6.09 mmol, 0.55 mL) was added and after 15 minutes the mixture was heated to reflux. After 48 hours the reaction was quenched with water and extracted with ethyl acetate (4x). The organic phases were combined, dried (MgSO4), filtered and concentrated. The residue was subjected to flash chromatography (hexane followed with 1% ethyl acetate) to afford 0.35 g (37%) of 2-(1-butoxy)thiazole as an amber oil.

Workup

  1. temperaturewas heated to reflux
  2. customAfter 48 hours the reaction was quenched with water
  3. extractionextracted with ethyl acetate (4x)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-11895ee0a9ec497f86c0ada80d951274
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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