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

HRID 1440511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1440511
O[C@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]([O:5][CH3:6])=O.[O-]S(C(F)(F)F)(=O)=O.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.N1[C:43](C)=[CH:42][CH:41]=[CH:40][C:39]=1[CH3:45].C1([SH:52])C=CC=CC=1>>[CH3:6][O:5][C:3](=[S:52])[C@H:2]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:45]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

6

Edukt 5

HCID 79372,6-LutidineHCID 7969ThiophenolHCID 67749Trifluoromethanesulfonic anhydrideHCID 2758875Trifluoromethanesulfonate2×HCID 10465463(R)-methyl 2-hydroxydecanoate

Produkt 1

HCID 54261197(S)-Methyl-2-phenylthiodecanoate

Versuchsvorschrift

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).

Aufarbeitung

  1. customThe desired (S)-methyl-2-phenylthiodecanoate (1.48 g) was purified by silica gel chromatography (1.00 gm, 3.39 mmol, 69%)
  2. custom[α]D =-101.2° (c=1, MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-0692a810bd824f429c81cda77a3d31f1
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498786

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