benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester

Base Information

Chemical Name:benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester
CAS No.:863444-93-3
Molecular Formula:C₂₀H₂₄O₄
Molecular Weight:328.408
Hs Code.:

Synonyms:benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester

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Chemical Property of benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester

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Technology Process of benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester

There total 10 articles about benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester 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: 86.0%

: 863445-05-0
Benzoic acid (S)-2-[(4S,5S)-2,2-dimethyl-5-((E)-2-methyl-4-trimethylsilanyl-but-1-en-3-ynyl)-[1,3]dioxolan-4-yl]-1-methyl-ethyl ester

: 863444-93-3
benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1039/b505980a

Reference yield:

: 863444-55-7
benzoic acid 2-(2,2-dimethyl-5-prop-1-ynyl-[1,3]dioxolan-4-yl)-1-methyl-ethyl ester

: 863444-93-3
benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₃SnH / PdCl₂(PPh₃)2 / pentane / 0.75 h

1.2: 144 mg / I₂ / CH₂Cl₂ / 0.33 h / -78 - 20 °C

2.1: iPrNH₂ / Pd(PPh₃)4 / 0.08 h / 20 °C

2.2: 97 percent / CuI; iPrNH₂ / 1 h

3.1: 86 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

With tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; isopropylamine; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pentane; 2.2: Sonogashira coupling;
DOI:10.1039/b505980a

Reference yield:

: 863444-49-9
6-O-benzoyl-1,1-dibromo-5,7-dideoxy-3,4-O-isopropyliden-L-arabino-hept-1-ene

: 863444-93-3
benzoic acid 2-[2,2-dimethyl-5-(2-methyl-but-1-en-3-ynyl)[1,3]dioxolan-4-yl]-1-methyl-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / LDA / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: LDA / tetrahydrofuran; hexane / 0.05 h / -78 °C

2.2: 88 percent / HMPA / tetrahydrofuran; hexane / 2 h / -78 - -10 °C

3.1: Bu₃SnH / PdCl₂(PPh₃)2 / pentane / 0.75 h

3.2: 144 mg / I₂ / CH₂Cl₂ / 0.33 h / -78 - 20 °C

4.1: iPrNH₂ / Pd(PPh₃)4 / 0.08 h / 20 °C

4.2: 97 percent / CuI; iPrNH₂ / 1 h

5.1: 86 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

With tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; isopropylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; pentane; 4.2: Sonogashira coupling;
DOI:10.1039/b505980a