Bicyclo[4.2.0]octa-1,3,5-triene-7-ethanol, 3-methoxy-, 4-methylbenzenesulfonate

Base Information

• Chemical Name: Bicyclo[4.2.0]octa-1,3,5-triene-7-ethanol, 3-methoxy-, 4-methylbenzenesulfonate
• CAS No.: 60100-24-5
• Molecular Formula: C18H20O4S
• Molecular Weight: 332.42
• Mol file: 60100-24-5.mol

Synonyms:

Chemical Property of Bicyclo[4.2.0]octa-1,3,5-triene-7-ethanol, 3-methoxy-, 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[4.2.0]octa-1,3,5-triene-7-ethanol, 3-methoxy-, 4-methylbenzenesulfonate

There total 1 articles about Bicyclo[4.2.0]octa-1,3,5-triene-7-ethanol, 3-methoxy-, 4-methylbenzenesulfonate 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:

→ 2-(4-methoxybenzocyclobutenyl)ethyl p-toluenesulfonate (60100-24-5)

Guidance literature:

Alkohol 13, Tosylchlorid;

DOI:10.1021/ja00452a045

Reference yield: 97.0%

2-(4-methoxybenzocyclobutenyl)ethyl p-toluenesulfonate (60100-24-5) → 2-(4-methoxybenzocyclobutenyl)ethyl p-tolyl sulfone (99598-48-8)

Guidance literature:

With sodium 4-methylbenzenesulfinate; sodium iodide; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1016/S0040-4020(01)96631-1

Reference yield:

2-(4-methoxybenzocyclobutenyl)ethyl p-toluenesulfonate (60100-24-5) → cis-4,5-(4-methoxybenzo)-1β,7aβ-(5α-methoxy-2α-methoxymethylfuro)-7-phenylthio-2-p-toluenesulfinylhydrindane (99598-54-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / sodium p-toluenesulfinate, sodium iodide / dimethylformamide / 2 h / 80 °C

2: 1.) lithium diisopropylamide; 2.) hexamethylphosphoramide / 1.) tetrahydrofuran, -78 deg C, 1 h; 2.) tetrahydrofuran, -78 deg C, 2 h

3: 1.) 60percent sodium hydride; 2.) 10percent hydrochloric acid / 1.) benzene, r.t., 30 min; 2.) 8 h, r.t., water

4: 1.) methanesulfonyl chloride / 1.) pyridine, r.t., 1 h; 2.) 3 h, r.t.

5: 23 percent / 1,2-dichloro-benzene / 4 h / 180 °C

6: 88 percent / 1.75M diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C

7: 87 percent / boron trifluoride-diethyl ether / 15 h / Ambient temperature

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; sodium 4-methylbenzenesulfinate; sodium iodide; lithium diisopropyl amide; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1,2-dichloro-benzene;

DOI:10.1016/S0040-4020(01)96631-1

Downstream raw materials:

2-(4-methoxybenzocyclobutenyl)ethyl p-tolyl sulfone

4β-<2-(4-methoxybenzocyclobutenyl)-1-p-toluenesulfinyl>-ethyl-5α-methoxymethyl-furan-2-one

(4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one

4β-<2-(4-methoxybenzocyclobutenyl)-1-p-toluenesulfinyl>-ethyl-5α-methoxymethyl-3-phenylthiomethylenefuran-2-one