1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene

Base Information

• Chemical Name: 1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene
• CAS No.: 944382-78-9
• Molecular Formula: C₁₇H₂₁ClO₂
• Molecular Weight: 292.806
• Mol file: 944382-78-9.mol

Synonyms:1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene

Chemical Property of 1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene

There total 11 articles about 1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene 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: 94.0%

1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-oxo-ethan-1'''-yl)cyclohex-6-ene (944382-77-8) + acetylenemagnesium bromide (4301-14-8) → 1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene (944382-78-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1039/b703373g

Reference yield:

2-(2-hydroxyethyl)-cyclohexan-1-one (10198-27-3) → 1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene (944382-78-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 0.85 g / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

2.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 2 h / -78 - 20 °C

2.2: 99 percent / tetrahydrofuran / 3 h / -78 - 0 °C

3.1: (bis)-triphenylphosphine palladium (II) chloride / tetrahydrofuran; pentane / 5 h / Heating

4.1: 6.1 g / pyridinium p-toluenesulfonate / methanol / 48 h / 20 °C

5.1: 96 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 6 h / 0 °C

6.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

7.1: 94 percent / N-chlorosuccinimide; triphenylphosphine; potassium carbonate / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 94 percent / potassium carbonate / methanol / 16 h / 20 °C

9.1: 76 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 94 percent / tetrahydrofuran / 0.5 h / 20 °C

With dmap; N-chloro-succinimide; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; triethylamine; diisopropylamine; triphenylphosphine; (bis)-triphenylphosphine palladium (II) chloride; In tetrahydrofuran; methanol; dichloromethane; pentane; 3.1: Stille coupling reaction;

DOI:10.1039/b703373g

Reference yield:

2-(2'-tert-butyldimethylsilyloxy-ethan-1'-yl)-cyclohexan-1-one (145386-47-6) → 1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-hydroxy-but-3'''-yn-1'''-yl)cyclohex-6-ene (944382-78-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 2 h / -78 - 20 °C

1.2: 99 percent / tetrahydrofuran / 3 h / -78 - 0 °C

2.1: (bis)-triphenylphosphine palladium (II) chloride / tetrahydrofuran; pentane / 5 h / Heating

3.1: 6.1 g / pyridinium p-toluenesulfonate / methanol / 48 h / 20 °C

4.1: 96 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 6 h / 0 °C

5.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

6.1: 94 percent / N-chlorosuccinimide; triphenylphosphine; potassium carbonate / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 94 percent / potassium carbonate / methanol / 16 h / 20 °C

8.1: 76 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 94 percent / tetrahydrofuran / 0.5 h / 20 °C

With dmap; N-chloro-succinimide; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; triethylamine; diisopropylamine; triphenylphosphine; (bis)-triphenylphosphine palladium (II) chloride; In tetrahydrofuran; methanol; dichloromethane; pentane; 2.1: Stille coupling reaction;

DOI:10.1039/b703373g

upstream raw materials:

1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-oxo-ethan-1'''-yl)cyclohex-6-ene

acetylenemagnesium bromide

2-(2-hydroxyethyl)-cyclohexan-1-one

2-(2'-tert-butyldimethylsilyloxy-ethan-1'-yl)-cyclohexan-1-one

Downstream raw materials:

1-[5'-(3''-chloro-propan-1''-yl)-2'-furanyl]-2'-(2'''-oxo-but-3'''-yn-1'''-yl)cyclohex-6-ene

1-[5'-(3''-iodo-propan-1''-yl)-2'-furanyl]-2'-(2'''-oxo-but-3'''-yn-1'''-yl)cyclohex-6-ene