Hydrogen Sulfide → 2-Methyl-1-sulfanylheptan-2-OL

Participants

Reaction Steps

Hydrogen sulfide gas was bubbled into a solution of 5 (3.84 g, 30 mmol) in tetrahydrofuran (30 mL) containing diisopropylamine (21 mL, 150 mmol) for one hour and the reaction mixture was stirred at room temperature for 68 hours. It was diluted with ether and washed with 10% aqueous hydrogen chloride, saturated sodium bicarbonate solution, and saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo; 1.2 g of 1-mercapto-2-methylheptan-2-ol 6 was obtained after HPLC purification. IR (neat): 3600-3200 cm-1 (br); PMR (CDCl3): δ 2.67 (s, 1H), 2.57 (s, 1H), 2.17 (s, 1H), 1.70-1.20 (m, 9H), 1.22 (s, 3H), and 0.90 (t, 3H).

Provenance & Evidence