Ethanethiol → 1-Adamantyl (Ethylthio)methyl Ketone

Participants

Reaction Conditions

Reaction Steps

Ethyl mercaptan (5.76 ml., 4.83 g., 0.078 mol) in 250 ml. THF was cooled to -70°. n-Butyllithium (50 ml. of 1.55M in hexane, 0.078 mol) was added over 10 minutes at that temperature. The mixture was then allowed to warm to 10°, recooled to -70°, and 1-adamantyl bromomethyl ketone (20 g., 0.078 mol) in 125 ml. THF added over. The mixture was stirred 15 minutes at -70° C., stripped to one fifth volume, diluted to 600 ml. with ether, washed 2×200 ml. saturated NH4Cl, 3×150 ml. H2O and 1×200 ml. brine, dried over MgSO4 and stripped to yield title product as an oil, 18.5 g. 1H-nmr (300 MHz) 1.2 (t, 3H), 1.6-2.1 (m, 15H), 2.5 (q, 2H), 3.35 (s, 2H).

Provenance & Evidence