exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one

Base Information

• Chemical Name: exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one
• CAS No.: 82740-93-0
• Molecular Formula: C₁₇H₂₂O₅S
• Molecular Weight: 338.425
• Mol file: 82740-93-0.mol

Synonyms:exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one

Chemical Property of exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one

There total 2 articles about exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one 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:

cis-3-(2-hydroxyethyl)-4-(2-hydroxy-2-propyl)-3-methylcyclobutene (82740-90-7) → exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one (82740-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

2: 1.) borane-THF, 2.) 3 M sodium hydroxide, 30percent hydrogen peroxide, 3.) 4-(dimethylamino)pyridine

With dmap; sodium hydroxide; borane-THF; dihydrogen peroxide; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/ja00384a040

Reference yield:

cis-1,5,5-trimethyl-4-oxabicyclo<4.2.0>oct-7-en-3-one (82740-91-8) + p-toluenesulfonyl chloride (98-59-9) → exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one (82740-93-0)

Guidance literature:

With dmap; sodium hydroxide; borane-THF; dihydrogen peroxide; Yield given. Multistep reaction;

DOI:10.1021/ja00384a040

Reference yield: 85.0%

exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octan-3-one (82740-93-0) → endo-3-hydroxy-exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octane (82740-94-1)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/ja00384a040

upstream raw materials:

cis-1,5,5-trimethyl-4-oxabicyclo<4.2.0>oct-7-en-3-one

p-toluenesulfonyl chloride

cis-3-(2-hydroxyethyl)-4-(2-hydroxy-2-propyl)-3-methylcyclobutene

Downstream raw materials:

endo-3-hydroxy-exo-7-<(p-tolylsulfonyl)oxy>-1,5,5-trimethyl-4-oxabicyclo<4.2.0>octane