2,6-Lutidine → HCID 54204795, compound

Participants

Reaction Steps

(S)-Methyl lactate (0.571 g, 5.27 mmol) was carried through the reaction sequence of Example 5 with triflic anhydride (1.02 ml, 6.05 mmol) and 2,6-lutidine (0.71 ml, 6.05 mmol) in 11 ml of CH3CN. Hexanethiol (1.02 ml, 6.84 mmol) and TEA (1.91 ml, 13.7 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 (R)-methyl-2-hexylthiopropionate as a clear yellow oil (0.933 g, 4.56 mmol, 86%). [α]D =+130.0° (c=1, MeOH). Anal. Calcd. for C10H20O2S: C, 58.78; H, 9.87: Found: D, 58.76; H, 9.99%.

Provenance & Evidence