2-(Trimethylsilyl)thiazole

Colorless to light yellow liqui

To a mixture of n-BuLi (2.5 M in hexane, 24 mL) and 18 mL of ether, a solution of 5.03 g thiazole dissolved in 59 mL of ether was added dropwise at -78 °C. After 30 min, TMSCl (6.41 g) dissolved in 59 mL of ether was added at -78 °C. The reaction mixture was stirred at -78 °C for 1 h and allowed to warm up to rt. The mixture was washed with saturated aHC0To a mixture of n-BuLi (2.5 M in hexane, 24 mL) and 18 mL of ether, a solution of 5.03 g thiazole dissolved in 59 mL of ether was added dropwise at -78 °C. After 30 min, TMSC1 (6.41 g) dissolved in 59 mL of ether was added at -78 °C. The reaction mixture was stirred at -78 °C for 1 h and allowed to warm up to rt. The mixture was washed with saturated NaHC0{0203] 2-(TriraethyisiJyl)t at)le (18). A 500-mL, four-necked, round- bottomed flask, containing a magnetic stirring bar, was equipped with two 1 0- raL, pressure-equalizing dropping funnels and a low-temperature thermometer. The anh apparatus was filled with argon and kept under a slightly positive pressure during the entire reaction. The flask was charged with 80 mL of freshly distilled Et jO and 42 mL (67 mmol) of a 1.6 M solution of -BuLi in hexane. One of the two dropping funnels was charged with 5.5 mL (10 g, 6 mmol) of 2- bromoihiazoe in 20 ml, of EfcO and the other with 7.7 ml (6.6 g, 61 mmol) of chorotrimethylsilane in 20 mL of EtjO. The reaction flask was cooled to -78 in an acetone bath. While ihe solution in the flask was stirred, 2~bromot azole was added dropwise over a period of I h. After 20 mm of additional stirring, ehiorotrimethylsilane was added dropwise over 30 min and the stirring was continued for a period of i h at -78 'C. The resulting mixture was then allowed to wa m up to room temperature. A satd aq aHCO' was added and the mixture was transferred into a i L separatory funnel. The organic layer was recovered and the aqueous layer was extracted with two 200-raL portions of E0. The combined organic layer was dried (NajSO ), filtered, and concentrated under diminished pressure with the external bath iemperature not exceeding 40 °C. The residue was distilled from a 1 -mL flask at diminished pressure in a Classen apparatus. The distillation was carried out under diminished pressure at 45 A 500-mL, four-necked, round-bottomed flask, containing a magnetic stirring bar, was equipped with two 1 00-mL, pressure- equalizing dropping funnels and a low-temperature thermometer. The anh apparatus was filled with argon and kept under a slightly positive pressure during the entire reaction. The flask was charged with 80 mL of freshly distilled Et20 and 42 mL (67 mmol) of a 1.6 M solution of n-BuLi in hexane. One of the two dropping funnels was charged with 5.5 mL (10 g, 61 mmol) of 2-bromothiazole in 20 mL of Et20 and the other with 7.7 mL (6.6 g, 61 mmol) of chlorotrimethylsilane in 20 mL of Et20. The reaction flask was cooled to —78 °C in an acetone bath. While the solution in the flask was stirred, 2-bromothiazole was added dropwise over a period of 1 h. After 20 mm of additional stirring, chiorotrimethylsilane was added dropwise over 30 mill and the stirring was continued for a period of 1 h at —78 °C. The resulting mixture was then allowed to warm up to room temperature. A satd aq NaHCO3 was added and the mixture was transferred into a 1 L separatory funnel. The organic layer was recovered and the aqueous layer was extracted with two 200-mL portions of Et20. The combined organic layer was dried (Na2SO4), filtered, and concentrated under diminished pressure with the external bath temperature not exceeding 40 °C. The residue was distilled from a 100-mL flask at diminished pressure in a Claisen apparatus. The distillation was carried out under diminished pressure at 45 °C after a forerun at 25°C consisting mainly of bromobutane was collected. The pure product 3 was isolated as a colorless oil: yield 7.3 g (76percent); ‘H NMR (CDC13) ö 0.39 (s, 12H), 7.50 (1H, d, J= 3.0 Hz) and 8.09 (1H, d, J= 2.9 Hz); ‘3C NMR (CDC13) ö 1.03, 127.3, 145.6 and 174.2.

Molecular Weight:157.31
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:157.03814706
Monoisotopic Mass:157.03814706
Topological Polar Surface Area:41.1
Heavy Atom Count:9
Complexity:99.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes