656836-55-4

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 688-73-3 tri-n-butyl-tin hydride 
• 78999-25-4 (C₆H₅CH₂CH₂CH(OH))Sn(C₄H₉)3 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 123294-06-4 3-(1-methoxymethoxy-3-phenylpropyl)cyclohexanone 
• 123312-61-8 3-(1-methoxymethoxy-3-phenylpropyl)cyclopentanone 
• 128756-22-9 4-Methoxymethoxy-6-phenyl-hexanoic acid trimethylhydrazide 
• 128756-27-4 4-Methoxymethoxy-3-methyl-6-phenyl-hexanoic acid trimethylhydrazide 
• 128756-17-2 4-Methoxymethoxy-6-phenyl-1-(2,2,6,6-tetramethyl-piperidin-1-yl)-hexan-1-one 
• 112606-95-8 5-(1-phenylethyl)-2-tetrahydrofuranone 
• 102519-59-5 trans-4-hydroxy-3-methyl-6-phenylhexanoic lactone 
• 102519-59-5 cis-4-hydroxy-3-methyl-6-phenylhexanoic lactone 
• 91898-11-2 1-methyloxymethoxy-3-phenylpropane 

Relevant academic research and scientific papers

Synthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals

Although transfer of electrophilic alkoxyl ("RO+") from organic peroxides to organometallics offers a complement to traditional methods for etherification, application has been limited by constraints associated with peroxide reactivity and stability. We now demonstrate that readily prepared tetrahydropyranyl monoperoxyacetals react with sp3 and sp2 organolithium and organomagnesium reagents to furnish moderate to high yields of ethers. The method is successfully applied to the synthesis of alkyl, alkenyl, aryl, heteroaryl, and cyclopropyl ethers, mixed O,O-acetals, and S,S,O-orthoesters. In contrast to reactions of dialkyl and alkyl/silyl peroxides, the displacements of monoperoxyacetals provide no evidence for alkoxy radical intermediates. At the same time, the high yields observed for transfer of primary, secondary, or tertiary alkoxides, the latter involving attack on neopentyl oxygen, are inconsistent with an SN2 mechanism. Theoretical studies suggest a mechanism involving Lewis acid promoted insertion of organometallics into the O-O bond.

Stereospecific palladium/copper cocatalyzed cross-coupling of α-alkoxy- and α-aminostannanes with acyl chlorides

Stille-type cross-coupling between α-alkoxy(amino)stannanes and acyl chlorides affords α-hetero-substituted ketones in moderate to good yields when cocatalyzed by Pd and Cu(I) salts. The reaction is applicable to a wide range of tin compounds, especially those bearing α-electron-withdrawing groups such as benzoyloxy or acetyloxy, although some ethers (e.g., MOM) are also satisfactory. Aromatic acid chlorides give the best yields. Coupling of chiral α-alkoxystannanes, readily available by BINAL-H asymmetric reduction of acylstannanes, proceeds with retention of configuration.