Ammonium Chloride → HCID 86731004, compound

Participants

Reaction Steps

To a suspension of methoxymethyltriphenylphosphonium chloride (1350 g, 3.90 mol) in anhydrous benzene (12 L), a solution of sodium tert-pentoxide (435 g, 3.90 mol) in anhydrous benzene (4 L) was added slowly under nitrogen atmosphere. The resulting red solution was stirred for 15 minutes at ambient temperature. Then, a solution of methyl 3-oxocyclobutanecarboxylate (250 g, 1.95 mol) in anhydrous benzene (1 L) was added slowly and the reaction mixture was heated at 70° C. for 2 hours. Saturated aqueous ammonium chloride (˜4 L) was added to the reaction mixture and extracted with diethyl ether (5 L). The organic layer was washed with water (5 L×2), brine (5 L), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography over silica gel (mesh 60-120; eluent: 10% diethyl ether in hexane) to afford the title compound as a pale yellow liquid. 1H NMR (300 MHz, CDCl3): δ 2.89-2.92 (m, 2H), 2.96-3.0 (m, 2H), 3.14-3.17 (m, 1H), 3.56 (s, 3H), 3.70 (s, 3H), 5.81-5.83 (m, 1H). GC-MS: [M]+ m/z=156.

Provenance & Evidence