Imidazole → 2-[3-(tert-Butyldimethylsilanyloxy)propyl]thiazole

HRID 1096827Notes

Reaction equation

HRID 1096827 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][CH2:20][CH2:21][OH:22]>C1COCC1>[Si:5]([O:22][CH2:21][CH2:20][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 178291513-(1,3-Thiazol-2-yl)propan-1-ol

Product 1

HCID 225033152-[3-(tert-Butyldimethylsilanyloxy)propyl]thiazoleYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBDMS-Cl (10.74 g, 71.2 mmol) and imidazole (5.38 g, 76.8 mmol) were added to a solution of 3-thiazol-2-yl-propan-1-ol (10.0 g 69.8 mmol) in THF (350 mL). Stirring was continued at rt overnight. The reaction mixture was partitioned between aq. sat. NH4Cl and Et2O. The aq. layer was extracted again with Et2O, the combined org. extracts were dried over MgSO4, filtered, and solvents were removed in vacuo. Purification of the crude by FC(CH2Cl2/MeOH 95:5) yielded the title compound as an orange oil (13.00 g, 72%). LC-MS: tR=1.05 min, ES+: 258.24.

Workup

  1. customThe reaction mixture was partitioned between aq. sat. NH4Cl and Et2O
  2. extractionThe aq. layer was extracted again with Et2O
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customsolvents were removed in vacuo
  6. customPurification of the crude by FC(CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-38a93eaa8b474fb3898229bff6e86118
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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