Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid, 3-bromo-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-, phenylmethyl ester

Base Information

• Chemical Name: Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid, 3-bromo-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-, phenylmethyl ester
• CAS No.: 87598-81-0
• Molecular Formula: C23H31BrO3Si
• Molecular Weight: 463.487
• Mol file: 87598-81-0.mol

Synonyms:

Chemical Property of Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid, 3-bromo-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid, 3-bromo-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-, phenylmethyl ester

There total 3 articles about Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid, 3-bromo-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-, phenylmethyl ester 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: 54.0%

1-[(tert-butyldimethylsilyl)oxy]-2-methyl-1,3-cyclohexadiene (87598-77-4) + bromopropynoic acid benzyl ester (87598-76-3) → 3-bromo-1-<(tert-butyldimethylsilyl)oxy>-2-(carbobenzyloxy)-6-methylbicyclo<2.2.2>octadiene (87598-81-0)

Guidance literature:

With 2-hydroxyresorcinol; for 12h; Ambient temperature;

DOI:10.1021/jo00174a008

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3-bromo-1-<(tert-butyldimethylsilyl)oxy>-2-(carbobenzyloxy)-6-methylbicyclo<2.2.2>octadiene (87598-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / potassium hydride / tetrahydrofuran / 1.) 35 deg C, 2.) room temp., 5 min

2: 54 percent / pyrogallol / 12 h / Ambient temperature

With potassium hydride; 2-hydroxyresorcinol; In tetrahydrofuran;

DOI:10.1021/jo00174a008

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → 3-bromo-1-<(tert-butyldimethylsilyl)oxy>-2-(carbobenzyloxy)-6-methylbicyclo<2.2.2>octadiene (87598-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / p-toluenesulfonic acid monohydrate / benzene / 21 h / Heating

2: 54 percent / pyrogallol / 12 h / Ambient temperature

With toluene-4-sulfonic acid; 2-hydroxyresorcinol; In benzene;

DOI:10.1021/jo00174a008

upstream raw materials:

1-[(tert-butyldimethylsilyl)oxy]-2-methyl-1,3-cyclohexadiene

bromopropynoic acid benzyl ester

tert-butyldimethylsilyl chloride

benzyl alcohol

Downstream raw materials:

1-<(tert-butyldimethylsilyl)oxy>-2-(carbobenzyloxy)-3,6-dimethylbicyclo<2.2.2>octadiene

1-<(tert-butyldimethylsilyl)oxy>-2-(carbobenzyloxy)-6-methyl-3-<3(S)-methyl-4-pentenyl>bicyclo<2.2.2>octadiene

benzyl 2-hydroxy-3-methyl-6-<3(S)-methyl-4-pentenyl>benzoate

benzyl 2-<(tert-butyldimethylsilyl)oxy>-3-methyl-6-<3-(S)-methyl-4-pentenyl>benzoate