Imidazole → 2-[2-(tert-Butyldimethylsilanyloxy)ethoxymethyl]thiazole

HRID 1096821Notes

Reaction equation

HRID 1096821 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].N1C=CN=C1.[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH2:19][O:20][CH2:21][CH2:22][OH:23]>C1COCC1>[Si:5]([O:23][CH2:22][CH2:21][O:20][CH2:19][C:15]1[S:14][CH:18]=[CH:17][N:16]=1)([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 451216842-(Thiazol-2-ylmethoxy)ethanol

Product 1

HCID 667839212-[2-(tert-Butyldimethylsilanyloxy)ethoxymethyl]thiazoleYield 544.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBDMS-Cl (2.4 g, 15.7 mmol) and imidazole (1.10 g, 16.9 mmol) were added to a sol. of 2-(thiazol-2-ylmethoxy)ethanol (2.45 g, 15.39 mmol) in THF (80 mL). The reaction mixture was stirred at rt over 15 h, partitioned between aq. sat. NH4Cl and Et2O. The phases were separated and the aq. layer was extracted with Et2O (2×). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil (22.93 g, 87%) that was not further purified. LC-MS: tR=1.06 min, ES+: 274.24.

Workup

  1. custompartitioned between aq. sat. NH4Cl and Et2O
  2. customThe phases were separated
  3. extractionthe aq. layer was extracted with Et2O (2×)
  4. dry with materiallayers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-e68aedde976741c8b6a34e37ea2a165e
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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