Acetone → 2-Thiazol-2-yl-propan-2-ol

HRID 1504795Notes

Reaction equation

HRID 1504795 reaction equation
C([Li])CCC.Br[C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[CH3:12][C:13]([CH3:15])=[O:14]>C(OCC)C>[S:8]1[CH:9]=[CH:10][N:11]=[C:7]1[C:13]([OH:14])([CH3:15])[CH3:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 764302-BromothiazoleHCID 178418339Butyllithium

Product 1

HCID 129928072-Thiazol-2-yl-propan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a −78° C. solution of n-butyllithium (2.5 M in diethyl ether, 160 ml, 0.40 mol) in diethyl ether (300 mL) was added slowly 2-bromo-1,3-thiazole (50 g, 0.30 mol). After 30 minutes, acetone (25 g, 0.43 mol) was added dropwise at −78° C. The reaction mixture was then warmed to ambient temperature, quenched with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (20% ethyl acetate/hexanes) to give 2-(1,3-thiazol-2-yl)propan-2-ol.

Workup

  1. customquenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was purified by chromatography on silica gel (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-29a914ca943648a2b446d4acd0c0d77a
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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