(R)-2-(1-(4-methoxyphenyl)-4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (R)-2-(1-(4-methoxyphenyl)-4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1570511-05-5
• Molecular Formula: C₂₃H₃₁BO₃
• Molecular Weight: 366.308

Synonyms:

Chemical Property of (R)-2-(1-(4-methoxyphenyl)-4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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Technology Process of (R)-2-(1-(4-methoxyphenyl)-4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 1 articles about (R)-2-(1-(4-methoxyphenyl)-4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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:

bis(pinacol)diborane (73183-34-3) → (S)-2-(1-(4-methoxyphenyl)-4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane + (R)-2-(1-(4-methoxyphenyl)-4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1570511-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(l) iodide; triphenylphosphine; lithium methanolate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere; Sealed tube

2: (3aR,8aR)-N,N,2,2-tetramethyl-4,4,8,8-tetra-p-tolyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-amine; palladium diacetate; potassium hydroxide / 1,4-dioxane / 12 h / 20 °C / Sealed tube; Inert atmosphere

With copper(l) iodide; (3aR,8aR)-N,N,2,2-tetramethyl-4,4,8,8-tetra-p-tolyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-amine; lithium methanolate; palladium diacetate; triphenylphosphine; potassium hydroxide; In 1,4-dioxane; N,N-dimethyl-formamide; 2: |Suzuki Coupling;

DOI:10.1021/ja500029w

Reference yield:

para-iodoanisole (696-62-8) + 4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane (1379610-52-2) + (R)-2-(1-(4-methoxyphenyl)-4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1570511-05-5)

Guidance literature:

With (3aR,8aR)-N,N,2,2-tetramethyl-4,4,8,8-tetra-p-tolyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-amine; palladium diacetate; potassium hydroxide; In 1,4-dioxane; at 20 ℃; for 12h; Overall yield = 73 %; enantioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1021/ja500029w

upstream raw materials:

bis(pinacol)diborane

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