反应详情

In accordance with the procedure of Furstner (Angew. Chem. Int. Ed., 2002, 41, 609-612), a solution of methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoate (334 mg, 1.0 mmol) and Fe(acac)3 in THF (6 mL) and NMP (0.56 mL) was treated with n-hexylmagnesium bromide (1.2 mL of a 2.0 M solution in Et2O, 2.4 mmol) at room temperature. After 30 min, the mixture was diluted with Et2O (20 mL) and quenched with 1 N aqueous HCl (5 mL). The phases were separated and the organic phase was washed with water (2×15 mL) and brine (15 mL), then dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified on 40 g silica gel (100% hexanes→20% EtOAc/hexanes, gradient) to afford 206 mg (76%) of methyl 6-hexyl-1-naphthoate.

1. customquenched with 1 N aqueous HCl (5 mL)
2. customThe phases were separated
3. washthe organic phase was washed with water (2×15 mL) and brine (15 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified on 40 g silica gel (100% hexanes→20% EtOAc/hexanes, gradient)