Ethyl (E)-(3-tert-butyldiphenylsiloxymethyl)-5-(trimethylsilyl)pent-2-en-4-ynoate

Base Information

Chemical Name:Ethyl (E)-(3-tert-butyldiphenylsiloxymethyl)-5-(trimethylsilyl)pent-2-en-4-ynoate
CAS No.:274908-69-9
Molecular Formula:C₂₇H₃₆O₃Si₂
Molecular Weight:464.752
Hs Code.:

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

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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 Ethyl (E)-(3-tert-butyldiphenylsiloxymethyl)-5-(trimethylsilyl)pent-2-en-4-ynoate

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Technology Process of Ethyl (E)-(3-tert-butyldiphenylsiloxymethyl)-5-(trimethylsilyl)pent-2-en-4-ynoate

There total 4 articles about Ethyl (E)-(3-tert-butyldiphenylsiloxymethyl)-5-(trimethylsilyl)pent-2-en-4-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: 72.0%

: 274908-64-4
Ethyl (Z)-4-[tert-butyl(diphenyl)siloxy]-3-{[(trifluoromethyl)sulfonyl]oxy}but-2-enoate

: 1066-54-2
trimethylsilylacetylene

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

Guidance literature:: With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 16h;
DOI:10.1055/s-2000-6366

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With copper(l) iodide; sodium 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;
DOI:10.1055/s-2000-6366

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

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