ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate

Base Information

• Chemical Name: ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate
• CAS No.: 912967-37-4
• Molecular Formula: C₂₁H₃₂O₄Si
• Molecular Weight: 376.568
• Mol file: 912967-37-4.mol

Synonyms:ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate

Chemical Property of ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate

There total 3 articles about ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate 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%

ethyl 5-(benzyloxy)-3-hydroxypentanoate (158414-68-7) + 4-trimethylsilanyl-but-2-ynyl 2,2,2-trichloroacetimidate (912967-75-0) → ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate (912967-37-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 2,4,6-tri-tert-butylpyrimidine; In cyclohexane; at 20 - 25 ℃; for 6h;

DOI:10.1021/ol061957v

Reference yield:

trimethyl(propargyl)silane (13361-64-3) → ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate (912967-37-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / diethyl ether; hexane / -78 - 0 °C

1.2: 89 percent / diethyl ether; hexane / 48 h / 20 °C

2.1: sodium / 0 - 25 °C

3.1: 67 percent / trimethylsilyl trifluoromethanesulfonate; 2,4,6-tri-tert-butylpyrimidine / cyclohexane / 6 h / 20 - 25 °C

With n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sodium; 2,4,6-tri-tert-butylpyrimidine; In diethyl ether; hexane; cyclohexane;

DOI:10.1021/ol061957v

Reference yield:

4-(trimethylsilyl)but-2-yn-1-ol (90933-84-9) → ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-ynyloxy)pentanoate (912967-37-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium / 0 - 25 °C

2: 67 percent / trimethylsilyl trifluoromethanesulfonate; 2,4,6-tri-tert-butylpyrimidine / cyclohexane / 6 h / 20 - 25 °C

With trimethylsilyl trifluoromethanesulfonate; sodium; 2,4,6-tri-tert-butylpyrimidine; In cyclohexane;

DOI:10.1021/ol061957v

upstream raw materials:

ethyl 5-(benzyloxy)-3-hydroxypentanoate

4-trimethylsilanyl-but-2-ynyl 2,2,2-trichloroacetimidate

trimethyl(propargyl)silane

4-(trimethylsilyl)but-2-yn-1-ol

Downstream raw materials:

(Z)-5-benzyloxy-3-(4-trimethylsilanyl-but-2-enyloxy)pentanal

(Z)-ethyl 5-benzyloxy-3-(4-trimethylsilanyl-but-2-enyloxy)pentanoate