Diisopropyl Ether → HCID 131721646, compound

Participants

Reaction Steps

Methyl (2Z,4E)-2-(methoxy-5-(3-methylbenzothiophen-2-yl)-2,4-pentadienoate and methyl (2Z,4E)-2-(methoxy-5-(3-methylbenzothiophen-2-yl)-2,4-pentadienoate. A solution of (E)-3-[2-(3-methylbenzothiophen-2yl)]-2-propenal (1 g, 5 mmol) in CH2Cl2 (30 ml) under nitrogen was treated with methoxycarbonylmethyl-2-methoxy triphenylphosphonium bromide (4.45 g, 10 mmol) and DBU (1.5 ml, 10 mmol). The reaction mixture was stirred at room temperature for 2 hours, washed with 10% aqueous HCl (5 ml), saturated solution of NaHCO3 (5 ml) and brine (5 ml), dried over Na2SO4 and evaporated under vacuum. The residue was purified by chromatography on silicagel (hexane/EtOAc 7/3) to afford, after trituration with isopropyl ether, methyl (2Z,4E)-2-methoxy-5-)3-methylbenzothiophen-2-yl)-2,4-pentiadienoate (380 mg, 1.32 mmol, yield 26.3%), m.p.=106-107° C., and methyl (2E,4E)-2-methoxy-5-(methylbenzothiophen-2-yl)-2,4-pentadienoate, (13 mg, 0.050 mmol, yield 1.0%), m.p.=91-92° C.

Provenance & Evidence