Pyrrolidine → (+/-)-Methyl 5-oxo-6-((tetrahydrofuran-3-yl)methylene)-5,6,7,8-tetrahydronaphthalene-2-carboxylate

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To a solution of methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (240 mg, 1.2 mmol) in methanol (3 mL) was added (±)-tetrahydrofuran-3-carboxaldehyde (240 mg, 2.4 mmol) and pyrrolidine (0.20 mL, 2.4 mmol). The solution was stirred for twenty hours at ambient temperature and for four hours at 45° C. The reaction was concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexane) provided (±)-methyl 5-oxo-6-((tetrahydrofuran-3-yl)methylene)-5,6,7,8-tetrahydronaphthalene-2-carboxylate as an orange oil (200 mg, 58% yield). LC/MS on 4.6×50 mm C-18 column, tR=2.52 minutes (10 to 90% acetonitrile/water over 4 minutes at 4 mL/minute with detection 254 nm, at 50° C.); ES-MS m/z 287 (M+H).

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