(Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate

Base Information

Chemical Name:(Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate
CAS No.:781662-92-8
Molecular Formula:C₂₃H₂₇IO₆
Molecular Weight:526.368
Hs Code.:

Synonyms:(Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate

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Chemical Property of (Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate

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Technology Process of (Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate

There total 5 articles about (Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate 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: 78.0%

: 346621-58-7
dimethyl 2-(3-phenylprop-2-yn-1-yl)malonate

: 781662-91-7
(Z)-1-bromo-3-iodo-4-(tetrahydropyran-2-yloxy)but-2-ene

: 781662-92-8
(Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate

Guidance literature:: dimethyl 2-(3-phenylprop-2-yn-1-yl)malonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

(Z)-1-bromo-3-iodo-4-(tetrahydropyran-2-yloxy)but-2-ene; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/jo049114+

Reference yield:

: 64244-47-9
4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

: 781662-92-8
(Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Red-Al(R) / tetrahydrofuran; toluene / 1 h / 0 °C

1.2: 86 percent / I₂ / tetrahydrofuran; toluene / -78 - 20 °C

2.1: 84 percent / N-bromosuccinimide; Me₂S / CH₂Cl₂ / 2 h / -20 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 78 percent / tetrahydrofuran / 2 h / 20 °C

With N-Bromosuccinimide; dimethylsulfide; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo049114+

Reference yield:

: 591-50-4
iodobenzene

: 781662-92-8
(Z)-dimethyl 2-[3-iodo-4-(tetrahydropyran-2-yloxy)but-2-enyl]-2-(3-phenylprop-2-yn-1-yl)malonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / CuI; (PPh₃)2PdCl₂; Et₃N / CH₂Cl₂ / 12 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 78 percent / tetrahydrofuran / 2 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Sonogashira coupling;
DOI:10.1021/jo049114+