Imidazole → 2-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazole

HRID 244483Notes

Reaction equation

HRID 244483 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][OH:7].N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C(Cl)Cl>[Si:13]([O:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27952131,3-Thiazol-2-ylmethanol

Product 1

HCID 214805922-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazoleYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of thiazol-2-ylmethanol (1.00 g, 8.684 mmol) in CH2Cl2 was added imidazole (1.18 g, 17.4 mmol) followed by tert-butyldimethylsilyl chloride (1.70 g, 11.3 mmol). After 30 minutes, the mixture was quenched with 2 mL of MeOH and passed through a pad of silica gel eluting with CH2Cl2 (700 mL) and concentrated in vacuo to afford 2.01 g (100%) of the title compound.

Workup

  1. customthe mixture was quenched with 2 mL of MeOH
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88ca08a0697a4cb59eae2472cba07378
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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