(E)-5-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-PENT-2-ENOIC ACID ETHYL ESTER

Base Information

• Chemical Name: (E)-5-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-PENT-2-ENOIC ACID ETHYL ESTER
• CAS No.: 94844-33-4
• Molecular Formula: C13H26 O3 Si
• Molecular Weight: 258.433
• Hs Code.: 2931900090
• Mol file: 94844-33-4.mol

Synonyms:2-Pentenoicacid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester, (E)-

Chemical Property of (E)-5-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-PENT-2-ENOIC ACID ETHYL ESTER

Chemical Property:

• PSA: 35.53000
• LogP: 3.51760

Purity/Quality:

99% ^*data from raw suppliers

(E)-5-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-PENT-2-ENOIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (E)-5-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-PENT-2-ENOIC ACID ETHYL ESTER

There total 10 articles about (E)-5-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-PENT-2-ENOIC ACID ETHYL ESTER 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: 96.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → ethyl (E)-5-((tert-butyldimethylsilyl)oxy)pent-2-enoate (94844-33-4)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 23 ℃; for 0.5h; Schlenk technique;

3-(tert-butyldimethylsilanyloxy)propionaldehyde; In tetrahydrofuran; mineral oil; at 0 - 23 ℃; Schlenk technique;

DOI:10.1021/acs.orglett.0c03957

Reference yield: 82.0%

3-tert-butyldimethylsilyloxy-1-propanol (73842-99-6) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (E)-5-((tert-butyldimethylsilyl)oxy)pent-2-enoate (94844-33-4)

Guidance literature:

3-tert-butyldimethylsilyloxy-1-propanol; With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 0 - 20 ℃; for 4h;

ethyl (triphenylphosphoranylidene)acetate; In dichloromethane; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.tet.2019.04.001

Reference yield:

3-tert-butyldimethylsilyloxy-1-propanol (73842-99-6) → ethyl (E)-5-((tert-butyldimethylsilyl)oxy)pent-2-enoate (94844-33-4)

Guidance literature:

Multi-step reaction with 2 steps

1: PCC / CH₂Cl₂ / 20 °C

2: 13.2 g / benzene / 24 h / Heating

With pyridinium chlorochromate; In dichloromethane; benzene;

DOI:10.1002/chem.200500892

upstream raw materials:

triethyl phosphonoacetate

3-(tert-butyldimethylsilanyloxy)propionaldehyde

5-{[(tert-butyldimethyl)silyl]oxy}pent-2-ynoic acid ethyl ester

ethyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

(E)-5-(tert-butyldimethylsilanyloxy)pent-2-en-1-ol

Acetic acid (E)-(4R,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-7-oxo-hept-2-enyl ester

Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

(2R,3R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-bis-(4-methoxy-benzyloxy)-pentan-1-ol