(E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate

Base Information

Chemical Name:(E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate
CAS No.:1352850-72-6
Molecular Formula:C₂₃H₂₅NO₃
Molecular Weight:363.456
Hs Code.:

Synonyms:(E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate

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Chemical Property of (E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate

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Technology Process of (E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate

There total 4 articles about (E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate 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: 63.0%

: 1313599-49-3
t-butyl-3-(prop-1-ynyl)-1H-indole-1-carboxylate

: 100-52-7
benzaldehyde

: 1352850-72-6
(E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate

Guidance literature:: With formic acid; Ru(O₂CCF₃)2(CO)(PPh₃)2; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 65 ℃; for 20h; optical yield given as %de; regioselective reaction; Inert atmosphere;
DOI:10.1002/chem.201101554

Reference yield:

: 120-72-9
indole

: 1352850-72-6
(E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere

1.2: 1 h / Inert atmosphere

2.1: dmap / dichloromethane / 16 h / Inert atmosphere

3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

4.1: formic acid; Ru(O₂CCF₃)2(CO)(PPh₃)2; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 20 h / 65 °C / Inert atmosphere

With dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; Ru(O₂CCF₃)2(CO)(PPh₃)2; tetra-(n-butyl)ammonium iodide; triethylamine; potassium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Sonogashira coupling;
DOI:10.1002/chem.201101554

Reference yield:

: 26340-47-6
3-Iodo-1H-indole

: 1352850-72-6
(E)-tert-butyl 3-(1-hydroxy-1-phenylbut-2-en-2-yl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: dmap / dichloromethane / 16 h / Inert atmosphere

2: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

3: formic acid; Ru(O₂CCF₃)2(CO)(PPh₃)2; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 20 h / 65 °C / Inert atmosphere

With dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; Ru(O₂CCF₃)2(CO)(PPh₃)2; tetra-(n-butyl)ammonium iodide; triethylamine; In tetrahydrofuran; dichloromethane; 2: Sonogashira coupling;
DOI:10.1002/chem.201101554