2,6-Lutidine → HCID 22859446, compound

Participants

Reaction Steps

(R)-Methyl lactate (0.553 g, 5.31 mol) was carried through the reaction sequence of Example 5 with triflic anhydride (1.03 ml, 6.11 mmol) and 2,6-lutidine (0.74 ml, 6.38 mmol) in 10 ml of CH3CN. Thiophenol (0.73 ml, 6.91 mmol) and TEA (1.93 ml, 13.8 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-phenylthiopropionate as a clear yellow oil (0.511 g, 2.60 mmol, 49%). [α]D =-165.4° (c=1.2, MeOH). 1H NMR δ7.43 (m, 2H), 7.29 (m, 3H), 3.78 (q, 1H, J =7.12 Hz), 3.65 (s, 3H)), 1.47 (d, 3H, J=7.12 Hz); 13C NMR δ172.87, 133.15, 133.01, 128.92, 128.00, 52.11, 45.07, 17.43.

Provenance & Evidence