tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate

Base Information

• Chemical Name: tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate
• CAS No.: 98830-99-0
• Molecular Formula: C₂₅H₄₁ClO₂Sn
• Molecular Weight: 527.762
• Mol file: 98830-99-0.mol

Synonyms:

Chemical Property of tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate

There total 3 articles about tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate 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: 41.0%

4-chlorobenzaldehyde (104-88-1) + tert-butyl α-(tri-n-butylstannyl)-α-(trimethylsilyl)acetate (98830-88-7) → tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate (98830-99-0,98830-94-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; byproducts: Me3SiOLi; lithium diisopropylamide in THF and HMPA was cooled in a dry ice-acetone bath, Sn-compound in THF was added dropwise; after 10 min, the mixt. was warmed to -23°C and stirred for 30 min, aldehyde was added at -78°C; aq. NH4Cl was added, mixt. extd. with petroleum ether, TLC on silica gel with petroleum ether-CH2Cl2;

Reference yield:

4-chlorobenzaldehyde (104-88-1) + tert-butyl α-(tri-n-butylstannyl)-α-(trimethylsilyl)acetate (98830-88-7) → (E)-tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate (98830-94-5,98830-99-0) + (Z)-tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate (98830-94-5,98830-99-0)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; under dry nitrogen, dropwise addn. of tert-butyl α-(tri-n-butylstannyl)-α-(trimethylsilyl)acetate to a soln. of LDA and HMPA at -78°C, stirring for 20 min at -42°C, recooling to -78°C, addn. of p-chlorobenzaldehyde; pouring into hexanes after 10 min, washing sequentially (aq. NH4Cl, water), drying (Na2SO4), concg., prep. TLC (SiO2, 50% CH2Cl2 in hexanes), elem. anal.; 74 % yield of 48:52 E:Z mixture;

DOI:10.1016/0022-328X(93)80069-N

Reference yield:

4-chlorobenzaldehyde (104-88-1) + tert-butyl α-(tri-n-butylstannyl)-α-(trimethylsilyl)acetate (98830-88-7) → (E)-tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate (98830-94-5,98830-99-0) + (Z)-tert-butyl 2-(tri-n-butylstannyl)-3-(4-chlorophenyl)-2-propenoate (98830-94-5,98830-99-0)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; under dry nitrogen, dropwise addn. of tert-butyl α-(tri-n-butylstannyl)-α-(trimethylsilyl)acetate to a soln. of LDA and HMPA at -78°C, stirring for 20 min at -42°C, recooling to -78°C, addn. of p-chlorobenzaldehyde; pouring into hexanes after 10 min, washing sequentially (aq. NH4Cl, water), drying (Na2SO4), concg., prep. TLC (SiO2, 50% CH2Cl2 in hexanes), elem. anal.; 74 % yield of 48:52 E:Z mixture;

DOI:10.1016/0022-328X(93)80069-N

upstream raw materials:

4-chlorobenzaldehyde

tert-butyl α-(tri-n-butylstannyl)-α-(trimethylsilyl)acetate