methyl (3aR*,4R*)-4-(2-bromoethyl)-2,3,3a,4,5,6-hexahydro-5,5-dimethyl-2-oxo-1-pentalenecarboxylate

Base Information

• Chemical Name: methyl (3aR*,4R*)-4-(2-bromoethyl)-2,3,3a,4,5,6-hexahydro-5,5-dimethyl-2-oxo-1-pentalenecarboxylate
• CAS No.: 75424-58-7
• Molecular Formula: C₁₄H₁₉BrO₃
• Molecular Weight: 315.207
• Mol file: 75424-58-7.mol

Synonyms:methyl (3aR*,4R*)-4-(2-bromoethyl)-2,3,3a,4,5,6-hexahydro-5,5-dimethyl-2-oxo-1-pentalenecarboxylate

Chemical Property of methyl (3aR*,4R*)-4-(2-bromoethyl)-2,3,3a,4,5,6-hexahydro-5,5-dimethyl-2-oxo-1-pentalenecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3aR*,4R*)-4-(2-bromoethyl)-2,3,3a,4,5,6-hexahydro-5,5-dimethyl-2-oxo-1-pentalenecarboxylate

There total 1 articles about methyl (3aR*,4R*)-4-(2-bromoethyl)-2,3,3a,4,5,6-hexahydro-5,5-dimethyl-2-oxo-1-pentalenecarboxylate 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:

4,4-dimethylcyclopent-2-ene-1-one (22748-16-9) → methyl (3aR*,4R*)-4-(2-bromoethyl)-2,3,3a,4,5,6-hexahydro-5,5-dimethyl-2-oxo-1-pentalenecarboxylate (75424-58-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (Bu₃P-CuI)4 / 1.) THF, -45 deg C, 15 min, -> 20 deg C, 1 h, 2.) THF, HMPA, room temperature, 1 h

2: TsOH-H₂O / toluene / 3 h / Heating

3: 1.) BH₃-THF, 2.) 30percent H₂O₂, aq. NaOH / 1.) THF, 0 deg C, 15 min, room temperature, 1.5 h, 2.) THF, MeOH, 40-50 deg C, 1 h

4: triethylamine / diethyl ether / 3 h / Ambient temperature

5: 1.25 g / lithium bromide / acetone / 6 h / Heating

6: 880 mg / sodium methoxide / methanol / 2 h / 0 °C

With sodium hydroxide; borane-THF; tetrakis{iodo(tributylphosphine)copper(I)}; dihydrogen peroxide; sodium methylate; toluene-4-sulfonic acid; triethylamine; lithium bromide; In methanol; diethyl ether; acetone; toluene;

DOI:10.1021/ja00404a026

upstream raw materials:

4,4-dimethylcyclopent-2-ene-1-one