Water → 6-Octyl-3,4-dihydronaphthalen-1(2H)-one

Participants

Reaction Steps

9-BBN (0.5 M solution in THF, 20.2 mL, 10.1 mmol) was added to 1-octene (1.6 mL, 10.1 mmol) at room temperature. The solution was stirred, at room temperature, overnight. After this time, K3PO4 (2.93 g, 13.8 mmol), Pd(Ph3P)4 (191 mg, 0.17 mmol, 1.8 mol %), KBr (1.2 g, 10.1 mmol) and degassed H2O (0.18 mL, 10 mmol) were added. This was followed by a solution of compound 2 (2.7 g, 9.2 mmol) in dry degassed THF (10 mL). The reaction mixture was heated at 65° C. under argon for 2 hours. After cooling, the solution was acidified to pH 1 and extracted into EtOAc (100 mL). The aqueous layer was re-extracted with EtOAc (50 mL) and the combined organics washed with H2O (20 mL) and brine (40 mL). The organic layer was dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 5% EtOAc in hexanes) to provide 1.93 g of compound 3 (82%).

Provenance & Evidence