Stannane, tributyl[4-(1,1-dimethylethyl)-1-(methoxymethoxy)cyclohexyl]-, trans-

Base Information

• Chemical Name: Stannane, tributyl[4-(1,1-dimethylethyl)-1-(methoxymethoxy)cyclohexyl]-, trans-
• CAS No.: 89746-17-8
• Molecular Formula: C₂₄H₅₀O₂Sn
• Molecular Weight: 489.37
• Mol file: 89746-17-8.mol

Synonyms:

Chemical Property of Stannane, tributyl[4-(1,1-dimethylethyl)-1-(methoxymethoxy)cyclohexyl]-, trans-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Stannane, tributyl[4-(1,1-dimethylethyl)-1-(methoxymethoxy)cyclohexyl]-, trans-

There total 5 articles about Stannane, tributyl[4-(1,1-dimethylethyl)-1-(methoxymethoxy)cyclohexyl]-, trans- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

tri-n-butyltin lithium (4226-01-1) + chloromethyl methyl ether (107-30-2) + 4-tercbutyl-cyclohexanone (98-53-3) → cis-4-tert-butyl-O-(methoxymethyl)-1-(tri-n-butylstannyl)cyclohexanol (89746-17-8,89726-83-0) + trans-4-tert-butyl-O-(methoxymethyl)-1-(tri-n-butylstannyl)cyclohexanol (89726-83-0,89746-17-8)

Guidance literature:

With N,N-dimethyl-aniline; In tetrahydrofuran; Ar; Bu3SnLi THF cooled to -40 °C; substrate added (30 s) in THF; stirred (15 min); poured in NH4Cl-soln. and petroleum ether; org. layer washed (brine), dried (Na2SO4); filtered; concd.; CH2Cl2 added; addn. ClCH2OCH3, aniline (16h, room temp.); poured into petroleum ether; washed (0.5 N HCl, water, Na2CO3-soln.); drying of org. layer (Na2SO4); filtered; concd.; chromd. (silica gel; ethyl acetate/petroleum ether 0.5:99.5); elem. anal.;;

DOI:10.1021/ja00211a024

Reference yield: 56.0%

tri-n-butyltin lithium (4226-01-1) + chloromethyl methyl ether (107-30-2) + 4-tercbutyl-cyclohexanone (98-53-3) → cis-4-tert-butyl-O-(methoxymethyl)-1-(tri-n-butylstannyl)cyclohexanol (89746-17-8,89726-83-0) + trans-4-tert-butyl-O-(methoxymethyl)-1-(tri-n-butylstannyl)cyclohexanol (89726-83-0,89746-17-8)

Guidance literature:

With N,N-dimethyl-aniline; In tetrahydrofuran; Ar; Bu3SnLi THF cooled to -40 °C; substrate added (30 s) in THF; stirred (15 min); poured in NH4Cl-soln. and petroleum ether; org. layer washed (brine), dried (Na2SO4); filtered; concd.; CH2Cl2 added; addn. ClCH2OCH3, aniline (16h, room temp.); poured into petroleum ether; washed (0.5 N HCl, water, Na2CO3-soln.); drying of org. layer (Na2SO4); filtered; concd.; chromd. (silica gel; ethyl acetate/petroleum ether 0.5:99.5); elem. anal.;;

DOI:10.1021/ja00211a024

Reference yield:

n-butyllithium (109-72-8,29786-93-4) + tri-n-butyltin lithium (4226-01-1) + chloromethyl methyl ether (107-30-2) + 4-tercbutyl-cyclohexanone (98-53-3) → cis-4-tert-butyl-O-(methoxymethyl)-1-(tri-n-butylstannyl)cyclohexanol (89746-17-8,89726-83-0) + trans-4-tert-butyl-O-(methoxymethyl)-1-(tri-n-butylstannyl)cyclohexanol (89726-83-0,89746-17-8)

Guidance literature:

With N,N-dimethyl-aniline; In tetrahydrofuran; diethyl ether; under argon; Bu3SnLi reacts at -78 °C with substrate in ether; dissolution in THF; cooled to -78 °C; addition of nBuLi (slight excess) over 1 min; stirring 10 min;; TLC; protection as methoxymethyl ether; NMR of 93:7 ratio of stannane;;

DOI:10.1021/ja00211a024

upstream raw materials:

n-butyllithium

tri-n-butyltin lithium

chloromethyl methyl ether

4-tercbutyl-cyclohexanone

Downstream raw materials:

trans-4-tert-butyl-O-(methoxymethyl)cyclohexanol

cis-4-tert-butyl-O-(methoxymethyl)cyclohexanol

4-tert-butyl-1-(methoxymethoxy)-1-cyclohexene

4-tercbutyl-cyclohexanone

Refernces