4-(Dimethylamino)benzene-1-thiol → trans-2-[-3-n-Propylsulfonyl-4-{2-(4-Dimethylaminophenylthio)ethoxy}-5-methoxyphenyl}-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Participants

Reaction Steps

Trans-2-[3-n-propylsulfonyl-4-(2-bromoethoxy)-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (100 mg) (Step 30G) was added to a stirred solution of 4-dimethylaminothiophenol (76 mg, 0.5 mmol) and sodium hydride (56%; 20 mg, 0.5 mmol) in DMF (1 mL). The reaction mixture was stirred at room temperature for 20 min and partitioned between ethyl ether and water. The organic layer was separated, dried, and evaporated to a crystalline mass. Recrystallized from ethyl ether-hexane gave pure product: mp 113°-115° C.; NMR (CDCl3) δ 1.0 (t, CH2CH2CH3), 1.70 (m, CH2CH2CH3), 2.0 & 2.49 (2 m, H-3 & H-4), 3.0 [m, (CH3)2N], 3.4 (m, CH2CH2CH3), 3.84 3.88 & 3.9 (3 s, 3 OCH3), 4.30 (t, SCH2CH2O), 5.22 (m, H-2 & H-5), 6.62 (s, C5ArH), 7.23 & 7.47 (2 d, J=1.5 Hz, C2ArH), 7.42 (m, ArH).

Provenance & Evidence