1-Hexanethiol → HCID 54204796, compound

Participants

Reaction Steps

(R)-Methyl lactate (0.587 g, 5.55 mmol) was treated as described in Example 5 with triflic anhydride (1.07 ml, 6.38 mmol) and TEA (0.89 ml, 6.39 mmol) in 11 ml of CH3CN. Hexanethiol (1.07 ml, 7.21 mmol) and TEA (1.01 ml, 7.21 mmol) were added and the workup described in Example 5 followed by purification by silica gel chromatography using 25 to 1 hexane to ethyl acetate as eluent gave (S)-methyl-2-hexylthiopropionate as a clear yellow oil (0.737 g, 3.61 mmol, 65%). [α]D =-128° (c=1, MeOH); 1N NMR δ3.69 (s, 3H), 3.36 (q, 1H, J=7.19 Hz), 2.54 (m, 2H), 1.60-1.17 (m, 8H), 1.39 (d, 3H, J=7.19 Hz), 0.84 (t, 3H, J=6.79 Hz); 13C NMR δ173.35, 51.85, 40.70, 31.23, 31.13, 29.11, 28.36, 22.36. 17.00, 13.81.

Provenance & Evidence