Hydrochloric Acid → 2-(Tert-butyldimethylsilyloxymethyl)-4-bromothiazole

HRID 709838Notes

Reaction equation

HRID 709838 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1.N1C=CN=C1.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].Cl>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([CH2:7][O:8][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20])[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11041630(4-Bromo-1,3-thiazol-2-yl)methanol

Product 1

HCID 167365792-(Tert-butyldimethylsilyloxymethyl)-4-bromothiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-bromothiazol-2-yl)methanol (1.30 g) and imidazole (600 mg) in THF (10 mL) was added dropwise tert-butyldimethylchlorosilane (1.60 mL), and the mixture was stirred at room temperature for 1 hr. 1N Hydrochloric acid was added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.90 g) as a colorless oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-618f66ba255e432c8d4df778c0ed3d33
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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