Chlorotrimethylsilane → HCID 11461188, compound

Participants

Reaction Steps

To 32 (46 mg, 0.19 mmol) dissolved in hexanes was added triethylamine (43 μL, 0.31 mmol) and trimethylsilylchloride (36 μL, 0.29 mmol) and the solution was allowed to stir at room temperature for 4 h. The mixture was filtered over celite and evaporated to provide 5-methyl-5-octyl-4-trimethylsilanyloxy-5-H-thiopen-2-one which was redissolved in CH2Cl2 (0.4 mL). To this mixture was added isopropyl isocyanate (19.2 mL, 0.19 mmol) and the solution was allowed to stir at room temperature for 2 hours. NH4Cl(sat) (5 mL) was added and the mixture was extracted with CH2Cl2 (3×10 mL). The organics were combined, dried (MgSO4), filtered and evaporated to give crude 71. Flash chromatography (20% EtOAc/2% AcOH/Hexanes) gave pure 71 (35 mg, 60%). 1H NMR (300 MHz, CDCl3) δ 0.85 (t, J=7.0 Hz, 3H), 1.14-1.24 (m, 17H), 1.45 (m, 1H), 1.63 (s, 3H), 1.76-1.79 (m, 2H), 3.81-3.88 (m, 1H), 5.16 (d, J=7 Hz, 1H), 6.33 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 13.9, 20.4, 22.5, 22.8, 25.1, 25.9, 29.1, 29.3, 29.5, 31.8, 38.7, 44.0, 60.2, 111.6, 149.7, 176.2, 194.5.

Provenance & Evidence