反应详情

A solution of methyl 6-formyl-1-naphthoate (36 mg, 0.17 mmol) in THE (1.7 mL) was cooled to 0° C. and treated with n-pentylmagnesium bromide (0.1 mL of a 2.0 M solution in Et2O, 0.2 mmol). The cooling bath was removed and after stirring at room temperature for 1 h the reaction was quenched with 1 N aqueous HCl, diluted with water (10 mL) and extracted with EtOAc (3×10 The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified on 12 g silica gel (100% hexanes→40% EtOAc/hexanes, gradient) to afford 34 mg (71%) of methyl 6-(1-hydroxyhexyl)-1-naphthoate.

1. customThe cooling bath was removed
2. customwas quenched with 1 N aqueous HCl
3. additiondiluted with water (10 mL)
4. extractionextracted with EtOAc (3×10 The combined organic phase
5. dry with materialwas dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting residue was purified on 12 g silica gel (100% hexanes→40% EtOAc/hexanes, gradient)