(E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol

Base Information

Chemical Name:(E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol
CAS No.:274908-70-2
Molecular Formula:C₂₅H₃₄O₂Si₂
Molecular Weight:422.715
Hs Code.:

Synonyms:(E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol

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Technology Process of (E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol

There total 5 articles about (E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol 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: 81.0%

: 274908-69-9
Ethyl (E)-(3-tert-butyldiphenylsiloxymethyl)-5-(trimethylsilyl)pent-2-en-4-ynoate

: 274908-70-2
(E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 - 0 ℃; for 3h;
DOI:10.1055/s-2000-6366

Reference yield:

: 115869-43-7
(tert-butyldiphenylsilanyloxy)acetaldehyde

: 274908-70-2
(E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 75 percent / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 71 percent / trifluoroacetic anhydride; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -65 - 20 °C

3.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

3.2: 65 percent / tetrahydrofuran / 6.5 h / 20 - 55 °C

4.1: 72 percent / i-Pr₂NH; CuI / PdCl₂(PPh₃)2 / tetrahydrofuran / 16 h

5.1: 81 percent / DIBAL / CH₂Cl₂ / 3 h / -78 - 0 °C

With copper(l) iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; trifluoroacetic anhydride; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; hexane; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: Oxidation / 3.1: Metallation / 3.2: Substitution / 4.1: Substitution / 5.1: Reduction;
DOI:10.1055/s-2000-6366

Reference yield:

: 274908-66-6
Ethyl (Z)-4-[tert-Butyl(diphenyl)siloxy]-3-oxobutanoate

: 274908-70-2
(E)-3-[(tert-Butyldiphenylsiloxy)methyl]-5-(trimethylsilyl)pent-2-en-4-yn-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

1.2: 65 percent / tetrahydrofuran / 6.5 h / 20 - 55 °C

2.1: 72 percent / i-Pr₂NH; CuI / PdCl₂(PPh₃)2 / tetrahydrofuran / 16 h

3.1: 81 percent / DIBAL / CH₂Cl₂ / 3 h / -78 - 0 °C

With copper(l) iodide; sodium hydride; diisobutylaluminium hydride; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; 1.1: Metallation / 1.2: Substitution / 2.1: Substitution / 3.1: Reduction;
DOI:10.1055/s-2000-6366