Triethylamine → 4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]thiazole
Reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[CH:2]1.CCN(CC)CC.[Si:15](OS(C(F)(F)F)(=O)=O)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C(Cl)Cl.CCOC(C)=O>[Si:15]([O:7][CH2:6][C:4]1[N:3]=[CH:2][S:1][CH:5]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 1,3-thiazol-4-ylmethanol (311.4 mg, 2.7 mmol) in CH2Cl2 (15 mL) was added Et3N (1.9 mL, 13.6 mmol). The solution was cooled to −78° C. and TBSOTf (776 μL, 3.38 mmol) was added. The reaction was warmed to room temperature and stirred for 1 hour. Next, the reaction was diluted with EtOAc (75 mL) and washed with saturated NaHCO3, brine, 1N HCl, and brine (20 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (0 to 15% EtOAc/hexanes) to afford 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazole. Rf=0.28 (15% EtOAc/hexanes). LCMS=230.1 (M+1)+. 1H NMR (CDCl3, 600 MHz) δ 8.77 (d, J=2.0 Hz, 1H), 7.25 (m, 1H), 4.93 (d, J=1.1 Hz, 2H), 0.95 (s, 9H), 0.12 (s, 6H).
Workup
- temperatureThe reaction was warmed to room temperature
- washwashed with saturated NaHCO3, brine, 1N HCl, and brine (20 mL each)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography on silica gel (0 to 15% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-dedf44e7fc53431ebdac3cff1e39026d
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735435B2
Reaction notes
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