Diiodomethane → HCID 66588531, compound

Participants

Reaction Steps

To a vigorously stirred solution of ((1S,2R,3R,4R,6S)-4-(benzyloxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)-5-methylenecyclohexane-1,2,3-triyl)tris(oxy)tris(methylene)-tribenzene (34, 25 mg, 32.7 μmol) in anhydrous toluene (2 mL) under nitrogen at −10° C. was added 2M solution of dimethyl zinc (146 μL, 291 μmol) dropwise and stirred for 15 minutes. Diiodomethane (47 μL, 583 μmol) was added drop-wise and the resulting mixture was stirred over night. 40% product fonnation was observed. More dimethyl zinc (18 more equivalent in two batches over 48 hour period) and diiodomethane (35 equivalent in two batches over 48 hour period) were added and the reaction was 80% complete after 96 hours of reaction. Saturated solution of NH4Cl (1 mL) was added and the mixture was stirred for 30 minutes. The mixture was diluted with water (1 mL) and extracted into ethyl acetate (3×1 mL). The combined organic extracts were washed with 10% sulfuric acid (1.5 mL), saturated NaHCO3 (1.5 mL) and brine (1.5 mL), dried (Na2SO4), filtered and evaporated. Preparative TLC (9:1 hexane:ethyl acetate) afforded 85% compound 36 which was used directly in the next reaction.

Provenance & Evidence