4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: 4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 932711-21-2
• Molecular Formula: C₂₆H₂₂O₅
• Molecular Weight: 414.458
• Mol file: 932711-21-2.mol

Synonyms:4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester

Chemical Property of 4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester

There total 9 articles about 4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl 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: 75.0%

{2-[(4-methoxyphenoxy)methyl]-4-(methylethylidene)-5-oxo-2-2,3-dihydrofuryl}methyl 4-[2-(4-ethynylphenyl)ethynyl]benzoate (932711-37-0) → 4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester (932711-21-2)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; for 0.166667h;

DOI:10.1021/jm061289j

Reference yield:

1-iodo-4-(trimethylsilylethynyl)benzene (134856-58-9) → 4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester (932711-21-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / piperidine / PdCl₂(PPh₃)2; CuI / tetrahydrofuran / 3 h

2: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h

3: 440 mg / dimethylaminopyridine; bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride / CH₂Cl₂ / 1 h

4: 75 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.17 h

With piperidine; dmap; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Sonogashira coupling;

DOI:10.1021/jm061289j

Reference yield:

4-trimethylsilylethynyl aniline (75867-39-9) → 4-(4-ethynyl-phenylethynyl)-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester (932711-21-2)

Guidance literature:

Multi-step reaction with 5 steps

1: NaNO₂; HCl; KI

2: 65 percent / piperidine / PdCl₂(PPh₃)2; CuI / tetrahydrofuran / 3 h

3: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h

4: 440 mg / dimethylaminopyridine; bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride / CH₂Cl₂ / 1 h

5: 75 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.17 h

With piperidine; hydrogenchloride; dmap; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium iodide; sodium nitrite; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane; water; acetonitrile; 2: Sonogashira coupling;

DOI:10.1021/jm061289j

upstream raw materials:

{2-[(4-methoxyphenoxy)methyl]-4-(methylethylidene)-5-oxo-2-2,3-dihydrofuryl}methyl 4-[2-(4-ethynylphenyl)ethynyl]benzoate

4-[2-(4-ethynylphenyl)ethynyl]benzoic acid

5-(hydroxymethyl)-5-[(4-methoxyphenoxy)methyl]-3-(methylethylidene)-4,5-dihydrofuran-2-one

5-[(4-methoxyphenoxy)methyl]-3-(methylethylidene)-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one

Downstream raw materials:

4-{4-[4-(2-{2-[2-(bis-tert-butoxycarbonylmethyl-carbamoyloxy)-ethoxy]-ethoxy}-ethoxy)-phenylethynyl]-phenylethynyl}-benzoic acid 2-hydroxymethyl-4-isopropylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester

Refernces