Diethyl Ether → 1-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

Methyl triphenylphosphonium bromide (2.75 g, 7.70 mmol) was suspended in 50 mL of diethyl ether. At −10° C., nBuLi (3.08 mL, 7.70 mmol, 2.5M soln in hexanes) was added. This mixture was stirred for 35 m before cooling to −70° C. A solution of (R)-(+)-4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone (1) (1.0 g, 6.09 mmol) in 15 mL of ether was added via syringe. This mixture was warmed to 0° C. over 30 m and the stirred at rt for another 30 m. The solution was washed with brine (2×20 mL) dried over MgSO4, filtered and the solvent was removed. Chromatography on SiO2 with hexanes gave 0.82 g (83%) of the diene 2 as a clear colorless oil.

Provenance & Evidence