endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-3,8-diene

Base Information

• Chemical Name: endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-3,8-diene
• CAS No.: 115296-91-8
• Molecular Formula: C₁₉H₂₀O₅S
• Molecular Weight: 360.431

Synonyms:endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-3,8-diene

Chemical Property of endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-3,8-diene

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Technology Process of endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-3,8-diene

There total 5 articles about endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-3,8-diene 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%

acetic anhydride (108-24-7) + 4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.02,6>deca-4,8-dien-endo-3-ol (113728-77-1) → endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.02,6>deca-3,8-diene (115296-91-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 1.5h;

DOI:10.1016/S0040-4020(01)89179-1

Reference yield:

maleic anhydride (930-60-9) → endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.02,6>deca-3,8-diene (115296-91-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / 336 h

2: 1.) glacial acetic acid / 1.) DMF, 70 deg C, 2h; 2.) 0 deg C, 3 h; room temp. overnight

3: 90 percent / 1.) triethylamine / CH₂Cl₂ / 3 h / Ambient temperature

5: 75 percent / triethylamine, DMAP / CH₂Cl₂ / 1.5 h

With dmap; acetic acid; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4020(01)89179-1

Reference yield:

5-ethoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.02,6>deca-4,8-dien-3-one (112698-71-2) → endo-5-acetoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.02,6>deca-3,8-diene (115296-91-8)

Guidance literature:

Multi-step reaction with 2 steps

2: 75 percent / triethylamine, DMAP / CH₂Cl₂ / 1.5 h

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4020(01)89179-1

upstream raw materials:

acetic anhydride

4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-4,8-dien-endo-3-ol

maleic anhydride

5-ethoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

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