Thiazole → HCID 22716763, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of thiazole (5.0 g, 58.7 mmol) in THF (250 mL) was added n-butyllithium (2.5M in hexanes, 23.5 mL, 58.7 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 until completion, and quenched with a saturated aqueous solution of NH4Cl. 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 purified by flash chromatography (80% CH2Cl2/20% EtOAc) to yield (1,3-Thiazol-2-yl)[4-(methylthio)phenyl]methanol.

Provenance & Evidence