(R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene

Base Information

• Chemical Name: (R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene
• CAS No.: 1016652-36-0
• Molecular Formula: C₂₅H₃₆O₂Si
• Molecular Weight: 396.645
• Mol file: 1016652-36-0.mol

Synonyms:(R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene

Chemical Property of (R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene

There total 2 articles about (R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene 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: 85.0%

(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate (1016652-32-6) + methoxybenzene (100-66-3) → (R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene (1016652-36-0)

Guidance literature:

methoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

With copper(I) bromide dimethylsulfide complex; magnesium bromide; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate; In tetrahydrofuran; hexane; at 0 ℃; for 1h; optical yield given as %ee; regiospecific reaction;

DOI:10.1016/j.tet.2009.11.052

Reference yield:

(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate (1016652-32-6) + 2-methoxyphenylmagnesium bromide (16750-63-3) → (R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene (1016652-36-0) + (S,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene

Guidance literature:

2-methoxyphenylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; Cooling with ice;

(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate; In tetrahydrofuran; at -60 - -40 ℃; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol800300x

upstream raw materials:

(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate

2-methoxyphenylmagnesium bromide

methoxybenzene