Aluminium lithium hydride → 1,3-Propanedithiol, 2-ethyl-2-(mercaptomethyl)-

Participants

Reaction Conditions

Reaction Steps

Compound 3 was converted to the trithiol by reduction with lithium aluminum hydride. Under N2, compound 3 (1.0 g, 3.9 mmol) and LiAlH4 (0.89 g, 23.4 mmol) were added to a 50 mL three necked round bottom flask. After the reaction was cooled to −5° C., cold ethyl ether (30 mL) was added by syringe while stirring. The reaction continued stir for 3 h at −5° C., brought to room temperature and stirred overnight. Upon return, grey solids were present. The reaction was cooled then quenched by the slow addition of saturated ammonium chloride (20 mL). Solids were removed via vacuum filtration, and 2 M HCl (20 mL) was added to the mother liquor. The product, 4, was extracted into ethyl ether (3×50 mL), dried over anhydrous Na2SO4, filtered, and taken to dryness to yield a light yellow oil, which crystallized upon cooling. Yield: 584 mg, 82%. 1H NMR (CDCl3; 500 MHz) δ ppm: 0.82 (t, 3H, CH3), 1.18 (t, 3H, SH), 1.46 (q, 2H, CCH2), 2.58 (d, 6H, SCH2). 13C NMR (CDCl3; 125.8 MHz) δ ppm: 7.85 (CH3), 25.10 (CCH2), 28.80 (SCH2), 41.66 (C). ESI-MS (m/z) 181.12 (181.03 calcd for [M−H]− of [C6H14S3]).

Provenance & Evidence