tert-Butyldimethylsilyl chloride → 2-(tert-Butyldimethylsilyl)thiazole

HRID 1655076Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[C:12]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+]>CCOCC>[Si:16]([C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 2-bromothiazole (57.4 g) in ether (70 ml) was added slowly to a solution of n-butyllithium (1.6M solution in hexane, 241 ml) in ether (700 ml) under an atmosphere of argon, maintaining the temperature below -60° C. After stirring for 1 hour at -70° C., a solution of tert-butylchlorodimethylsilane (63.0 g) in ether (70 ml) was added slowly dropwise. The reaction mixture was then allowed to warm to ambient temperature and stirred for 16 hours. Saturated aqueous sodium bicarbonate solution was added, the layers were separated, and the aqueous phase extracted twice with ether. The combined organic phases were dried (MgSO4), concentrated, and the residue was purified by column chromatography, eluting with 25% ethyl acetate/hexane (v/v), and subsequent distillation to give 2-tert-butyldimethylsilylthiazole (Q) (46 g, 58% yield) as an oil (b.p. 88°-96° C. at 10 mm of mercury);

Workup

temperaturemaintaining the temperature below -60° C
temperatureto warm to ambient temperature
stirringstirred for 16 hours
customthe layers were separated
extractionthe aqueous phase extracted twice with ether
dry with materialThe combined organic phases were dried (MgSO4)
concentrationconcentrated
customthe residue was purified by column chromatography
washeluting with 25% ethyl acetate/hexane (v/v), and subsequent distillation

Sources & evidence

ORD record: ord-e9c52635d1ad44c3824294bdbd1bad08
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05410064

Reaction notes

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