Phenylsulfonyl-2-butanone Ethylene Acetal

InChI= l/C12H16O4S/cl-12(15-8-9-16-12)7-10-17(13,14)11-5-3-2-4-6-1 l/h2-6H,7- 10H2,1H3 InChlKey = YVBGQPGMXFSZHS-UHFFFAOYAC [Pg.436]

Physical Data colorless crystals mp 33-34 °C or 41 2 °C. Preparative Method by the Michael addition of benzenesulfinic acid to 3-buten-2-one followed by acetalization with ethylene glycol. [Pg.436]

Synthesis of 2-Alkanones and 3-Alken-2-one. Monoalkylation of 4-phenylsulfonyl-2-butanone ethylene acetal 1 takes place at the position a to the phenylsulfonyl group on successive treatment with butyllithium and then with an alkyl halide (or tosylate). Deprotection of the acetal group and subsequent elimination of the benzenesulfinic acid moiety with a base transforms the monoalkylation product to the corresponding 3-alken-2-one (eq 1). A 2-alkanone is obtainable from the monoalkylation product by reductive desulfurization and subsequent acidic deprotection (eq 2) [Pg.436]

Alkane-2,5-dione Synthesis. On treatment with n-BuLi and an acyl chloride, (1) affords an a-acylated product, which easily undergoes reductive desulfurization with aluminum amalgam or sodium amalgam. Deprotection forms an alkane-2,5-dione (eq 3). - [Pg.436]

Synthesis of 6-Hydroxy-2-alkanones. The Uthio derivative of 1 reacts with a terminal epoxide to give a ring-opened product. Acidic deprotection of the product forms 6-hydroxy-2-alkanone which cyclizes to give a 5-lactol (eq 4). [Pg.436]

Big Chemical Encyclopedia