Methylparaben → Methyl 4-(3-tert-butoxycarbonyl-4-thiazolidinyl)methoxybenzoate

Participants

Reaction Steps

To a stirred solution of 3-tert-butoxycarbonyl-5-hydroxymethylthiazolidine (1.9 g, 8.7 mmol), methyl 4-hydroxybenzoate (1.3 g, 8.7 mmol), and Ph3P (3.2 g, 12.2 mmol) in THF (10 ml) was added DIAD (2.2 g, 10.4 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:9, v/v) as eluent to give methyl 4-(3-tert-butoxycarbonyl-4-thiazolidinyl)methoxybenzoate (1.6 g, 52%) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.49 (s, 9H), 3.11–3.19 (m, 2H), 3.88 (s, 3H), 4.04–4.31 (m, 3H), 4.61 (m, 2H), 6.96 (d, J=8.8 Hz, 2H), 7.98 (d, J=8.8 Hz, 2H).

Provenance & Evidence