145475-10-1

Upstream product

• 857551-59-8 3-(2,3-dihydro-benzofuran-2-yl)-propionic acid methyl ester 
• 64-17-5 ethanol 
• 230285-15-1 1-phenyl-5-(N-phthalimidoxy)-1-(2-tetrahydropyranyloxy)pentane 
• 230285-12-8 5-(tert-butyldiphenylsiloxy)-1-phenyl-1-pentanol 
• 230285-11-7 5-(tert-butyldiphenylsiloxy)-1-phenyl-1-pentanone 
• 230285-16-2 1-phenyl-5-(N-phthalimidoxy)-1-pentanol 
• 230285-14-0 1-phenyl-1-(2-tetrahydropyranyloxy)-5-pentanol 
• 1011-62-7 5-hydroxy-1-phenylpentan-1-one 
• 230285-17-3 1-(acetoxy)-1-phenyl-5-(N-phthalimidoxy)pentane 
• 821-09-0 n-Pent-4-enyl alcohol 
• 5371-52-8 2-hydroxytetrahydrofuran 
• 230285-13-9 5-(tert-butyldiphenylsiloxy)-1-phenyl-1-(2-tetrahydropyranyloxy)pentane 

Downstream Products

• 15212-27-8 2-benzyltetrahydrofuran 
• 1265632-28-7 C₁₁H₁₅ClO 
• 643754-28-3 (E)-3-(4-oxo-5-phenylpentylidene)tetrahydro-2H-pyran-2-one 
• 53707-97-4 4-oxo-5-phenylpentanal 

Relevant academic research and scientific papers

Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of Debromohamigeran e and Other Targets of Interest

A hydroxyl functional group positioned β to a pinacol boronate can serve to direct palladium-catalyzed cross-coupling reactions. This feature can be used to control the reaction site in multiply borylated substrates and can activate boronates for reaction that would otherwise be unreactive.

Cyclopropenium-activated cyclodehydration of diols

The dehydrative cyclization of diols to cyclic ethers via cyclopropenium activation is described. Using 2,3-diphenylcyclopropene and methanesulfonic anhydride, a series of 1,4-and 1,5-diols are rapidly cyclized to furnish tetrahydrofurans and tetrahydropyrans in high yield. Eleven total substrates are shown, including a gram scale cyclization of a diterpene derivative.

Inter- and intramolecular pathways for the formation of tetrahydrofurans from β-(phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism

β-(Phosphatoxy)alkyl radicals generated by photolysis of Barton PTOC esters in the presence of allyl alcohol and tert-butyl mercaptan undergo nucleophilic substitution followed by 5-exo-trig radical ring closure leading to tetrahydrofurans in good yield and with high trans selectivity. β- (Phosphatoxy)alkyl radicals obtained by intramolecular hydrogen 1,5- abstraction with an alkoxyl radical undergo nucleophilic displacement providing tetrahydrofurans. The ensemble of results, including the effects of leaving groups and substituents, strongly support a dissociative mechanism for these radical nucleophilic displacement reactions.

Generation of 2-Lithio-2-(trimethylsilyl)silacyclopentane and 2-Lithio-2-(phenylthio)silacyclopentane and Their Use for the Synthesis of 1,4-Butanediols and γ-Hydroxy Ketones

Treatment of 2-(trimethylsilyl)silacyclopentane with t-butyllithium in THF-HMPA gave 2-lithio-2-(trimethylsilyl)silacyclopentane in good yield.An addition of alkyl iodides to the lithium compound provided 2-alkyl-2-(trimethylsilyl)silacyclopentanes which

2-Lithio-2-trimethylsilyl-1-silacyclopentane as a Synthetic Equivalent of 1-Lithio-1,4-butanediol

Addition of alkyl iodide to 2-lithio-2-trimethylsilyl-1-silacyclopentane provided 2-alkyl-2-trimethylsilyl-1-silacyclopentane which was converted into 1-alkyl-1,4-butanediol by treatment with H2O2-KF and n-Bu4NF.