Tetrahydrofuran → HCID 22716773, compound

Temperature

-78 °C

To a −78° C. solution of thiazole (1.0 g, 12.0 mmol) in THF (100 ml) was added n-butyllithium (2.3M in hexanes, 5.3 mL, 12.3 mmol) dropwise and the resulting solution was stirred at −78° C. for 10 min. 4-(Methylthio)benzaldehyde (7.1 mL, 53.4 mmol) was then added at −78° C. The resulting mixture was stirred at r.t. 10 min. and cooled at −78° C. Then n-butyllithium (2.3M in hexanes, 5.3 mL, 12.3 mmol) was added dropwise and the resulting solution was stirred at 25° C. for 10 min and quenched with acetone (3.0 mL). The mixture was then diluted with EtOAc and HCl 10%, extracted and washed (NaHCO3 (sat.), brine). The organic phase was dried over MgSO4 and concentrated. The residue was then treated with MnO2 (20.4 g, 235 mmol) in CH2Cl2 (250 mL) and the reaction was stirred at r.t. overnight. The resulting mixture was then filtered through a plug of silica (EtOAc). Flash chromatography (90%CH2Cl2/10%EtOAc) yielded [5-(1-Hydroxy-1-Methylethyl)-1,3-thiazol-2-yl][4-(methylthio)phenyl)ketone.

1. stirringThe resulting mixture was stirred at r.t
2. temperature10 min. and cooled at −78° C
3. stirringthe resulting solution was stirred at 25° C. for 10 min
4. customquenched with acetone (3.0 mL)
5. additionThe mixture was then diluted with EtOAc and HCl 10%
6. extractionextracted
7. washwashed (NaHCO3 (sat.), brine)
8. dry with materialThe organic phase was dried over MgSO4
9. concentrationconcentrated
10. stirringthe reaction was stirred at r.t. overnight
11. filtrationThe resulting mixture was then filtered through a plug of silica (EtOAc)

ORD record

ord-d3fb908c2ec44b80bb7f44665c055cee

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06740666B2