dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate

Base Information

• Chemical Name: dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate
• CAS No.: 1644031-10-6
• Molecular Formula: C₂₁H₂₃ClO₅
• Molecular Weight: 390.864

Synonyms:dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate

Chemical Property of dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate

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Technology Process of dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate

There total 1 articles about dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)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: 62.0%

dimethyl 2,2-di(prop-2-ynyl)malonate (63104-44-9) + α,α-dimethyl-(4-chlorophenyl)acetaldehyde (20401-29-0) → dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate (1644031-10-6)

Guidance literature:

dimethyl 2,2-di(prop-2-ynyl)malonate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

α,α-dimethyl-(4-chlorophenyl)acetaldehyde; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1002/anie.201403990

Reference yield:

dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate (1644031-10-6) + benzenesulfenyl chloride (931-59-9) → C27H27ClO5S

Guidance literature:

With triethylamine; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201403990

Reference yield:

dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate (1644031-10-6) → dimethyl 2-[5-(4-chlorophenyl)-5-methyl-2-phenylsulfonylhexa-2,3-dienyl]-2-(prop-2-ynyl)malonate (1644030-59-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.201403990

upstream raw materials:

dimethyl 2,2-di(prop-2-ynyl)malonate

α,α-dimethyl-(4-chlorophenyl)acetaldehyde

Downstream raw materials:

dimethyl 2-[5-(4-chlorophenyl)-5-methyl-2-phenylsulfonylhexa-2,3-dienyl]-2-(prop-2-ynyl)malonate

14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,2,7,12,14-pentaene

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