methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester

Base Information

• Chemical Name: methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester
• CAS No.: 457071-59-9
• Molecular Formula: C₁₉H₂₂O₅S
• Molecular Weight: 362.447

Synonyms:methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester

Chemical Property of methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester

Chemical Property:

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Technology Process of methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester

There total 5 articles about methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl 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: 95.0%

methanesulfonyl chloride (124-63-0) + 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-yn-1-ol (457071-58-8) → methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester (457071-59-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.03.024

Reference yield:

2,3-dibromobenzene (583-53-9) → methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester (457071-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / Pd⁽⁰⁾; n-BuNH₂

2: 70 percent / Pd⁽⁰⁾; n-BuNH₂

3: 85 percent / NEt₃

With palladium; N-butylamine; triethylamine;

DOI:10.1016/S0960-894X(02)00029-X

Reference yield:

3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) → methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester (457071-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-butylamine / 3 h / Inert atmosphere; Reflux

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-butylamine / 10 h / Inert atmosphere; Reflux

3: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-butylamine; triethylamine; In dichloromethane; 1: Sonogashira coupling / 2: Sonogashira coupling;

DOI:10.1016/j.bmc.2011.03.024

upstream raw materials:

methanesulfonyl chloride

4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-yn-1-ol

2-bromo-1-(1-hydroxy-3-butyn-4-yl)benzene

2,3-dibromobenzene

Downstream raw materials:

2-{3-[2-(4-azido-but-1-ynyl)-phenyl]-prop-2-ynyloxy}-tetrahydro-pyran

C₂₄H₂₁NO₃S

C₂₃H₂₇NO₅

C₁₈H₁₉NO₄

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