Imidazole → 4-((Triisopropylsilyloxy)methyl)thiazole

HRID 2071064

Reaction equation

HRID 2071064 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[CH:2]1.[CH3:8][CH:9]([Si:11](Cl)([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH3:10].N1C=CN=C1>C(Cl)Cl>[CH:9]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[O:7][CH2:6][C:4]1[N:3]=[CH:2][S:1][CH:5]=1)([CH3:10])[CH3:8]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 2763215(1,3-Thiazol-4-yl)methanol

Product 1

HCID 686703364-((Triisopropylsilyloxy)methyl)thiazoleYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a DCM solution of thiazol-4-ylmethanol (Combi-Blocks)(1 g, 8.69 mmol) stirred at 0° C., were added TIPSCl (2.2 mL, 10.43 mmol) and imidazole (1.48 g, 21.72 mmol). The resulting mixture was then warmed to room temperature and stirred for overnight. The reaction was quenched with saturated aqueous NH4Cl solution, extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, concentrated to a residue which was purified by flash column to give 4-((triisopropylsilyloxy)methyl)thiazole (2 g). 1H NMR (300 MHz, CDCl3), d: 8.794 (m, 1H), 7.338 (m, 1H), 5.065 (s, 2H), 1.209 (m, 3H), 1.133 (d, J=6 Hz, 18H).

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl solution
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated to a residue which
  6. customwas purified by flash column

Sources & evidence

ORD record
ord-d1897134dd9a41cca40357542317dec7
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Linked notes

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