Imidazole → 2-((Tert-butyldimethylsilyloxy)methyl)thiazole
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
Product 1
Reagents, catalysts & solvents 1
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
- customthe mixture was quenched with 2 mL of MeOH
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-88ca08a0697a4cb59eae2472cba07378
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658637B2
Reaction notes
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