[2-(Methoxycarbonyl)-2-propenyl]tributylstannane

Base Information

• Chemical Name: [2-(Methoxycarbonyl)-2-propenyl]tributylstannane
• CAS No.: 132841-83-9
• Molecular Formula: C17H34O2Sn
• Molecular Weight: 389.166
• Mol file: 132841-83-9.mol

Synonyms:.methyl 2-(tri-n-butylstannylmethyl)propenoate;.(2-methoxycarbonyl-3-propenyl)tributylstannane;.methyl 2-[(tributylstannyl)methyl]acrylate;.2-(methoxycarbonyl)propenyltributylstannane;methyl 2-[(tributylstannyl)methyl]propenoate;.[2-(methoxycarbonyl)prop-2-enyl]tributylstannane;

Chemical Property of [2-(Methoxycarbonyl)-2-propenyl]tributylstannane

Chemical Property:

• PSA: 26.30000
• LogP: 5.56470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [2-(Methoxycarbonyl)-2-propenyl]tributylstannane

There total 3 articles about [2-(Methoxycarbonyl)-2-propenyl]tributylstannane 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: 67.0%

methanol (67-56-1) + tert-butyl phenyl(2-[(tributylstannyl)methyl]acryloyl)carbamate (1204430-96-5) → 2-(carbomethoxy)allyl tributyltin (132841-83-9)

Guidance literature:

With NaH; In methanol; soln. of Sn compd. in MeOH added to soln. of NaH in MeOH at 0°C, mixt. warmed to room temp., stirred for 1 h, aq. soln. of NH4Cl added; extn. with ethyl acetate, combined org. phases dried over Na2SO4, chromy. (SiO2, hexane/EtOAc 60/1); elem. anal.;

DOI:10.1016/j.jorganchem.2009.09.037

Reference yield:

tributyltin chloride (1461-22-9) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) → 2-(carbomethoxy)allyl tributyltin (132841-83-9)

Guidance literature:

methacrylic acid methyl ester; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 1h;

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

tributyltin chloride; In tetrahydrofuran; hexane; for 1h;

DOI:10.1002/chem.201403357

Reference yield:

2-<(4-methylphenylsulfonyl)methyl>propenoic acid methyl ester (126234-89-7) + tri-n-butyl-tin hydride (688-73-3) → 2-(carbomethoxy)allyl tributyltin (132841-83-9)

Guidance literature:

With catalyst: AIBN; In toluene; refluxing in toluene for 1 h;

DOI:10.1039/c39900001574

upstream raw materials:

2-<(4-methylphenylsulfonyl)methyl>propenoic acid methyl ester

tri-n-butyl-tin hydride

methanol

tert-butyl phenyl(2-[(tributylstannyl)methyl]acryloyl)carbamate

Downstream raw materials:

(4S,5S)-4-(Benzyl-ethoxycarbonyl-amino)-2-methylene-5-triisopropylsilanyloxy-hexanoic acid methyl ester

Refernces

• 1、 Suzuki, Takamasa,Atsumi, Jun-ichi,Sengoku, Tetsuya,Takahashi, Masaki,Yoda, Hidemi. "Indium-catalyzed enantioselective allylation of aldehydes with β-carbonyl allylstannanes: An efficient synthetic method for chiral α-methylene-γ-lactones". . p. 128 - 136. Retrieved 2010/09/18.