Carbonate Ion → trans-2-[3-(2-Oxopropylsulfonyl)-4-n-propoxy-5-{3-(3-pyridyl)propoxy}phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Participants

Reaction Conditions

Reaction Steps

3-(3-Bromopropyl)pyridine hydrobromide (51 mg, 0.18 mmol) was added to a solution of trans-2-[3-(2-oxopropylsulfonyl)-4-n-propoxy-5-(2-hydroxy)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (50.8 mg, 0.1 mmol) [Example 1, Step L] in DMF (2 mL) containing postassium carbonate (28 mg, 0.2 mmol), and the reaction mixture was heated at 70° C. for 1 h. The product was extracted with ethyl ether in the usualy way and purified by preparative TLC (hexane-ethyl acetate; 1:2, v/v) Rf 0.15; MS, m/z 628 (M+1)+. ; NMR (CDCl3) δ d 1.09 (t, J=7.5 Hz, CH2CH2CH3), 1.92 (m, CH2CH2CH3), 2.18 (m, CH2CH2CH2Pyr), 2.37 (s, CH2COCH3), 2.87 (t, CH2CH2CH2Pyr), 3.83 (s, OCH3 ), 3.88 (s, 2 OCH3), 4.08 (t, CH2CH2CH2Pyr), 4.18 (t, CH2CH2CH3), 4.48 (s, CH2CO), 5.13-5.27 (m, H-2 and H-5), 6.61 (s, 2 H, C5ArH).

Provenance & Evidence