Imidazole → HCID 11161185, compound

Participants

Reaction Steps

The hydroxy lactone of Example 8 (6.0 g, 42.2 mmol) was dissolved in dry dimethylformamide (10 ml) under nitrogen. Imidazole (4.78 g, 70.2 mmol) and then tert-butyldimethylsilyl chloride (7.05 g, 46.80 mmol) were added. The mixture was stirred at room temperature overnight and then partitioned between water (50 ml) and heptane (2×30 ml). The heptane extracts were dried (MgSO4), filtered and evaporated to give the crude product (10.5 g). This was crystallised from heptane (40 ml) at −15° C. to give the title compound as a white solid (7.60 g, 29.6 mmol, 70%); m.p. 48° C. (onset by DSC); Found: C, 61.1; H, 9.5. C13H24O3Si requires C, 60.9; H, 9.4%; vmax (Nujol) 1763 and 1644 cm−1; [α] +88.0° (c=1.0, CH2Cl2); 1HNMR(400 MHz, CDCl3) δ ppm5.94-5.80 (1 H, m), 5.18-5.06(2 H, m), 4.53 (1 H, t, J 3.5), 4.26 (1 H, dd, J 10,3), 4.17 (1 H, d, J 10), 2.60-2.35 (3 H, m), 0.89 (9 H, s), 0.10 (3 H, s) and 0.08 (3 H, s); m/z (GCMS, EI) 199 (M-tBu, 4%) and 117 (100).

Provenance & Evidence