Triphenylphosphine → HCID 10922629, compound

Participants

Reaction Steps

To a stirred solution of ethyl 4-hydroxy-3-methoxybenzoate (1.46 g, 7.44 mmol), N-Boc ethanolamine (1.19 g, 7.38 mmol), PPh3 (2.53 g, 9.65 mmol) in THF (30 mL) was added DIAD (1.90 mL, 9.65 mmol), and the resulting mixture was then heated under reflux overnight. The mixture was evaporated to give a crude gum. The crude product was dissolved in CH2Cl2 (20 mL) and TFA (20 mL). The resulting mixture was stirred for 2.5 hr at room temp. The mixture was concentrated in vacuo and the residue was made basic with sat. NaHCO3 and extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and evaporated to give the 1.61 g (90% for 2 steps ) ethyl 3-methoxy-4-(2-aminoethoxy)benzoate as a yellow oil. 1H-NMR (CDCl3) d 1.39 (t, 3 H, J=7.3 Hz), 3.14-3.17 (m, 2 H), 3.92 (s, 3 H), 4.09-4.11 (m, 2 H), 4.36 (q, 2 H, J=7.3 Hz), 6.89 (d, 1 H, J=8.3 Hz), 7.56 (d, 1 H, J=2.0 Hz), 7.66 (dd, 1 H, J=2.0, 8.3 Hz).

Provenance & Evidence