2,6-Lutidine → (S)-Methyl-2-phenylthiodecanoate

Beteiligte Stoffe

Reaktionsschritte

Following the procedure of Example 5, (R)-methyl 2-hydroxydecanoate (0.99 gm, 4.90 mmol) was converted to the triflate with triflic anhydride (0.95 ml, 5.65 mmol) and 2,6-lutidine (0.66 ml, 5.63 mmol). The triflate was displaced with thiophenol (0.62 ml, 5.88 mmol) in the presence of TEA (1.57 ml, 11.3 mmol). The desired (S)-methyl-2-phenylthiodecanoate (1.48 g) was purified by silica gel chromatography (1.00 gm, 3.39 mmol, 69%). [α]D =-101.2° (c=1, MeOH). 1H NMR δ7.41 (m, 2H), 7.25 (m, 3H), 3.63 (dd, 1H, J=6.8,8.3 Hz), 3.62 (s, 3H), 1.86 (m, 1H), 1.74 (m, 1H), 1.43-1.24 (m, 12H), 0.86 (t, 3H, J=6.8 Hz).

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