134749-87-4

Basic information

• Product Name: 2-(2-trimethylsilanylphenyl)-1,3-dioxolane
• Synonyms: 2-(2-trimethylsilanylphenyl)-1,3-dioxolane
• CAS NO: 134749-87-4
• Molecular Weight: 222.359
• Mol File: 134749-87-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-(2-trimethylsilanylphenyl)-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-trimethylsilanylphenyl)-1,3-dioxolane(134749-87-4)
• EPA Substance Registry System: 2-(2-trimethylsilanylphenyl)-1,3-dioxolane(134749-87-4)

Safety Data

• Hazardous Substances Data: 134749-87-4(Hazardous Substances Data)

Upstream product

• 17887-55-7 2-trimethylsilylbenzaldehyde 
• 107-21-1 ethylene glycol 

Downstream Products

• 43108-70-9 (2R*, 1'R*)-2-(hydroxy(phenyl)methyl)cyclopentanone 
• 43108-71-0 anti-2-<(hydroxy)(phenyl)methyl>cyclopentanone 

Relevant articles and documents

Asymmetric nucleophilic substitution of acetals

Benzaldehyde dimethylacetal (1) and 2-aryl-1,3-dioxolanes 5 react with organolithium reagents 2 in the presence of chiral ligands such as sparteine (3), 1-alkoxy-2-aminoethanes, or 1,2-dialkoxyethanes and BF3 to afford monosubstitution products in high yields and in up to 81% enantiomeric excess. The enantioselectivity is strongly influenced by steric effects in the acetal and in the reagent. The highest ee was achieved with 2-(2-isopropyl)-1,3-dioxolane (5c) on treatment with 2-ethylphenyllithium (2i) in the presence of sparteine. The approach was applied to the synthesis of enantioenriched (S)-(-)-neobenodine (17) with 49% ee.