Anisole → HCID 69334713, compound

Participants

Reaction Steps

A mixture of methyl 4-(1-tert-butoxycarbonylamino-2-methyl-2-propoxy)benzoate (460 mg, 1.42 mmol) and anisole (0.155 mL, 1.42 mmol) in CH2Cl2(15 mL) and TFA (3 mL) was stirred for 3 hr at room temp. The mixture was evaporated off. The residue was dissolved in CH2Cl2 (30 mL) and made basic by the addition of 0.5 N NaOH. The CH2Cl2 layer was separated, dried over Na2SO4, and evaporated. The residue was chromatographed on silica-gel with CH2Cl2 as eluent to give 370 mg (100%) methyl 4-(1-amino-2-methyl-2-propoxy)benzoate as a gum. 1H-NMR (CDCl3) δ 1.34 (s, 6H), 2.87 (s, 2H), 3.90 (s, 3H), 7.10 (d, J=8.8 Hz, 2H), 7.97 (d, J=8.8 Hz, 2H).

Provenance & Evidence