Triethylamine → 4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]thiazole

HRID 1994542

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

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-2a99fa1f3a634d1eb48ca5ea284c46c6
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652049B2

Linked notes

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