Diiodomethane → HCID 57779798, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried 250 mL round-bottom flask was fitted with a stirbar and septa and flushed with nitrogen. Diethyl zinc (12.0 mL, 1.0 M/hexanes, 12.0 mmol) was added and cooled to 0° C. Trifluoroacetic acid (0.90 mL, 11.7 mmol) was added in a careful, dropwise manner over 5 minutes, and the reaction was then stirred for 15 minutes. Methylene chloride (10 mL) and diiodomethane (1.20 mL, 14.9 mmol) were then added, and the reaction was stirred for an additional 20 minutes. A solution of the product of Step 1 (1.01 g, 4.19 mmol) in methylene chloride (20 mL) was then added, and the reaction was stirred overnight with gradual warming to room temperature. After 25 hours, the reaction was poured into saturated aqueous NH4Cl solution (50 mL) and extracted with methylene chloride (3×50 mL). The organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (0% to 20% ethyl acetate/hexanes linear gradient) to give the desired product.

Provenance & Evidence