Propanedioic acid, [4-[2-(1-octynyl)phenyl]-3-butynyl]-, 1,1-dimethylethyl ethyl ester

Base Information

• Chemical Name: Propanedioic acid, [4-[2-(1-octynyl)phenyl]-3-butynyl]-, 1,1-dimethylethyl ethyl ester
• CAS No.: 107586-23-2
• Molecular Formula: C₂₇H₃₆O₄
• Molecular Weight: 424.58
• Mol file: 107586-23-2.mol

Synonyms:

Chemical Property of Propanedioic acid, [4-[2-(1-octynyl)phenyl]-3-butynyl]-, 1,1-dimethylethyl ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propanedioic acid, [4-[2-(1-octynyl)phenyl]-3-butynyl]-, 1,1-dimethylethyl ethyl ester

There total 12 articles about Propanedioic acid, [4-[2-(1-octynyl)phenyl]-3-butynyl]-, 1,1-dimethylethyl ethyl 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: 26.0%

4-<2-(oct-1-ynyl)phenyl>but-3-ynyl toluene-p-sulphonate (121221-95-2) → 1-(but-3-en-1-ynyl)-2-(oct-1-ynyl)benzene (121221-97-4) + ethyl t-butyl 2-<4-<2-(oct-1-ynyl)phenyl>but-3-ynyl>malonate (107586-23-2)

Guidance literature:

With tert-Butyl ethyl malonate; potassium hydride; 1.) THF, 0 deg C, 5 min, 2.) 18-crown-6, 1,2-dimethoxyethane, 80 deg C, overnight;

Reference yield:

n-octyne (629-05-0) → ethyl t-butyl 2-<4-<2-(oct-1-ynyl)phenyl>but-3-ynyl>malonate (107586-23-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 62 percent / triphenylphosphine, palladium(II) acetate, triethylamine / 110 °C

2: 77 percent / triphenylphosphine / 1.) dichloromethane, 5 deg C, 1 h, 2.) 20 deg C, overnight

3: 68 percent / potassium t-amylate / hexane / 1.) 0 - 20 deg C, 30 min, 2.) 20 deg C, overnight

4: 1.) butyl-lithium / 1.) THF, -78 deg C, 2 h, 2.) 48 h

5: 52.5 percent / pyridine / 48 h / 0 °C

6: 1.) potassium hydride, 2.) 18-crown-6 / 1.) THF, 0 deg C, 5 min, 2.) 1,2-dimethoxyethane, 80 deg C, overnight

With pyridine; n-butyllithium; 18-crown-6 ether; palladium diacetate; potassium hydride; potassium 2-methylbutan-2-olate; triethylamine; triphenylphosphine; In hexane;

Reference yield:

1-octynylzinc chloride (68113-72-4) → ethyl t-butyl 2-<4-<2-(oct-1-ynyl)phenyl>but-3-ynyl>malonate (107586-23-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 37 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 60 °C

2: 77 percent / triphenylphosphine / 1.) dichloromethane, 5 deg C, 1 h, 2.) 20 deg C, overnight

3: 68 percent / potassium t-amylate / hexane / 1.) 0 - 20 deg C, 30 min, 2.) 20 deg C, overnight

4: 1.) butyl-lithium / 1.) THF, -78 deg C, 2 h, 2.) 48 h

5: 52.5 percent / pyridine / 48 h / 0 °C

6: 1.) potassium hydride, 2.) 18-crown-6 / 1.) THF, 0 deg C, 5 min, 2.) 1,2-dimethoxyethane, 80 deg C, overnight

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 18-crown-6 ether; potassium hydride; potassium 2-methylbutan-2-olate; triphenylphosphine; In tetrahydrofuran; hexane;

upstream raw materials:

tert-Butyl ethyl malonate

4-<2-(oct-1-ynyl)phenyl>but-3-ynyl toluene-p-sulphonate

n-octyne

2-(oct-1-yn-1-yl)benzaldehyde

Downstream raw materials:

t-butyl hydrogen 2-<4-<2-(oct-1-ynyl)phenyl>but-3-ynyl>malonate

Refernces