(E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate

Base Information

Chemical Name:(E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate
CAS No.:626249-42-1
Molecular Formula:C₂₅H₃₈O₃Si
Molecular Weight:414.66
Hs Code.:

Synonyms:(E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate

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Chemical Property of (E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate

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Technology Process of (E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate

There total 6 articles about (E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate 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: 56.0%

: 626249-41-0
methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate

: 626249-42-1
(E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate

Guidance literature:: methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate; With dmap; methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ja037423w

Reference yield:

: 928-90-5
5-hexyl-1-ol

: 626249-42-1
(E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / CuI; iPr₂NH; Pd(Ph₃)4 / tetrahydrofuran / 20 °C

2.1: 95 percent / PCC / CH₂Cl₂ / 5 h / 35 °C

3.1: iPr₂NH; n-BuLi / hexane; tetrahydrofuran / 0.58 h / -78 °C

3.2: 66 percent / tetrahydrofuran / 3 h / -78 °C

4.1: DMAP; Et₃N; MsCl / CH₂Cl₂ / 1 h / 0 - 20 °C

4.2: 56 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

With dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; methanesulfonyl chloride; triethylamine; diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja037423w

Reference yield:

: 130602-09-4
6-phenylhex-5-yn-1-al

: 626249-42-1
(E)-methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-7-phenylhept-2-en-6-ynoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: iPr₂NH; n-BuLi / hexane; tetrahydrofuran / 0.58 h / -78 °C

1.2: 66 percent / tetrahydrofuran / 3 h / -78 °C

2.1: DMAP; Et₃N; MsCl / CH₂Cl₂ / 1 h / 0 - 20 °C

2.2: 56 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

With dmap; n-butyllithium; methanesulfonyl chloride; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja037423w