(E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane

Base Information

• Chemical Name: (E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane
• CAS No.: 79707-80-5
• Molecular Formula: C₂₀H₂₆O₅S
• Molecular Weight: 378.489
• Mol file: 79707-80-5.mol

Synonyms:(E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane

Chemical Property of (E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane

There total 7 articles about (E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane 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: 91.0%

(E)-2-hydroxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane + acetyl chloride (75-36-5) → (E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane (79707-80-5)

Guidance literature:

With dmap; In dichloromethane; at 25 ℃; for 1h;

DOI:10.1021/ja00415a024

Reference yield:

3-(phenylsulfonyl)butan-2-one (53258-83-6) → (E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane (79707-80-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH, 2.) n-butyllithium / 1) 25 deg C, 2 h, THF; 2) hexane, 0 deg C (1 h), 25 deg C (90 min); 3) 0 deg C, 2.5 h

2: 86 percent / n-Bu₄NF, benzoic acid / tetrahydrofuran / 21 h / Heating

3: 91 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 25 °C

With dmap; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; benzoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00415a024

Reference yield:

(Z)-<(carboethoxy)methylidene>-2-hydroxycyclohexane (95713-78-3) → (E)-2-acetoxy<(4-(benzenesulfonyl)-3-oxopentyl)methylidene>cyclohexane (79707-80-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / imidazole / dimethylformamide / 2 h / 25 °C

2: 96 percent / diisobutylaluminum hydride / toluene; hexane / 1) -78 deg C, 1.5 h; 2) 25 deg C, 30 min

3: 84 percent / CCl₄, HMPA / diethyl ether / 1.5 h / 0 °C

4: 1.) NaH, 2.) n-butyllithium / 1) 25 deg C, 2 h, THF; 2) hexane, 0 deg C (1 h), 25 deg C (90 min); 3) 0 deg C, 2.5 h

5: 86 percent / n-Bu₄NF, benzoic acid / tetrahydrofuran / 21 h / Heating

6: 91 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 25 °C

With 1H-imidazole; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; benzoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00415a024

upstream raw materials:

acetyl chloride

3-(phenylsulfonyl)butan-2-one

(Z)-<(carboethoxy)methylidene>-2-hydroxycyclohexane

(E)-2-(tert-butyldimethylsiloxy)<(chloromethyl)methylidene>cyclohexane

Downstream raw materials:

2-(benzenesulfonyl)-3-(cyclohex-1-en-1-yl)-2-methylcyclopentanone

2-(benzenesulfonyl)-3-(cyclohex-1-en-1-yl)-2-methylcyclopentanone