Acetone → 5-Thiazolemethanol, 2-amino--alpha-,-alpha--dimethyl-

Temperatur

-78 °C

To a −78° C. solution of thiazol-2-amine (7.0 g, 69.9 mmol) in tetrahydrofuran (200 mL) was added a 10.0 M solution of butyllithium in hexane (14 mL, 140 mmol). The mixture was stirred at −78° C. for 1 hour and chlorotrimethylsilane (15.2 g, 140 mmol) was added dropwise. The mixture was allowed to warm up to −40° C., cooled to −78° C. and a 10.0 M solution of butyllithium in hexane (7.0, 70 mmol) was added. After 10 minutes, propan-2-one (8.12 g, 140 mmol) was added and the mixture was stirred for 12 hours. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with ether. The organic extract was dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.61 (s, 6H) 5.04-5.19 (brs, 2H) 6.89 (s, 1H); MS (ESI) m/z 159 (M+H)+.

1. temperatureto warm up to −40° C.
2. temperaturecooled to −78° C.
3. waitAfter 10 minutes
4. stirringthe mixture was stirred for 12 hours
5. customThe reaction mixture was quenched with saturated aqueous NH4Cl
6. extractionextracted with ether
7. extractionThe organic extract
8. dry with materialwas dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by column chromatography

ORD-Eintrag

ord-c2c66425f264471c891b75252e0cae04

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841334B2