Diethyl Ether → HCID 19027129, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-trimethylsilylthiazole (2.2 g, 13.9 mmoL) (J. Org. Chem., 1988, 53, 1748) in Et2O (12 mL) was added at -78° C., dropwise a solution of n-BuLi in hexanes (2.45m, 5.68 mL) and the solution was stirred for 30 min. A solution of keto ester from Naphthol 5, Step 3, (2.0 g, 8.05 mmoL) in Et2O (5 mL) was then added dropwise and the reaction was stirred at -78° C. for 1 hr. and warmed to r.t. A saturated NaHCO3 solution was added and the mixture was extracted with Et2O (2×), washed with H2O, dried over MgSO4, filtered and evaporated. The crude compound was purified by flash chromatography on silica gel eluting with hexanes: EtOAc (7:3) to afford directly the title alcohol as an oil.

Provenance & Evidence