Ammonium Hydroxide → HCID 66766023, compound

Participants

Reaction Steps

To a solution of 3-methoxy-5-bromotoluene (0.50 g, 2.49 mmol) in dry THF (8 mL) was added n-BuLi (1.71 mL, 2.74 mmol, 1.6 M in Hexane) dropwise at −78° C. After the reaction mixture was stirred for 15 min, Li2CuCl4 (0.1 mL, 0.1 mmol, 0.1 M in THF) was added, and the mixture was stirred for another 10 min at the same temperature. Then, a solution of (E,E)-farnesyl bromide (0.70 mL, 2.58 mmol) in THF (3 ml) was added over 0.5 hour and stirring was continued for 2 hours at −78° C. After the reaction was complete, the mixture was warmed to room temperature and saturated aqueous NH4Cl (20 mL) was added, followed by 10% NH4OH (40 mL) and Et2O (3×50 mL). The combined organic layer was washed with water, brine, and dried with Na2SO4. The crude product was purified by flash silica gel chromatography (hexanes/EtOAc 60:1, 30:1, 20:1 and 10:1) to yield compound 24 (658.1 mg, 78%) as a colorless oil.

Provenance & Evidence