Ammonium Chloride → HCID 86615477, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of the oil isolated in Step A (17.5 g, 65 mmol), and cuprous iodide (0.75 g) in THF (100 mL) at 0° C., a solution of allylmagnesium bromide in THF (2 M, 42 mL, 84 mmol) was added slowly while the temperature was maintained at about 5-10° C. The reaction mixture then was stirred at room temperature overnight. Aqueous saturated ammonium chloride solution (100 mL) was then added. The reaction mixture was stirred 30 min at room temperature and then extracted with ethyl acetate (200 mL). The organic solution washed with saturated ammonium chloride solution three times and with brine one time, and then was dried over sodium sulfate. The reaction mixture was then filtered and concentrated to yield a residue. The residue was purified by Kugelrohr distillation to yield a colorless oil (GC showed it contained 20% starting material, but the oil was used as is without further purification).

Provenance & Evidence