4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester

Base Information

• Chemical Name: 4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester
• CAS No.: 753497-85-7
• Molecular Formula: C₂₈H₂₉BrO₅
• Molecular Weight: 525.439
• Mol file: 753497-85-7.mol

Synonyms:4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester

Chemical Property of 4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester

There total 2 articles about 4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl 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: 43.0%

methyl 4-formylbenzoate (1571-08-0) + (5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one (753497-69-7) → 4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester (753497-85-7)

Guidance literature:

(5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.25h;

methyl 4-formylbenzoate; In tetrahydrofuran; at -78 ℃; for 0.5h;

With pyridine; dmap; acetic anhydride; at 80 ℃; for 1.5h;

DOI:10.1039/b404016c

Reference yield:

2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one → 4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester (753497-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 220 mg / Br₂ / CH₂Cl₂ / 0.4 h

2.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

2.2: tetrahydrofuran / 0.5 h / -78 °C

2.3: 43 percent / Ac₂O; 4-DMAP; pyridine / 1.5 h / 80 °C

With bromine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b404016c

Reference yield: 48.0%

4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester (753497-85-7) → 4(E)-[4-bromo-2(R)-hydroxy-(1(R)-hydroxy-5-phenylpentyl)-5-oxo-cyclopent-3-enylidenemethyl]-benzoic acid methyl ester + 4(Z)-[4-bromo-2(R)-hydroxy-(1(R)-hydroxy-5-phenylpentyl)-5-oxo-cyclopent-3-enylidenemethyl]-benzoic acid methyl ester

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1039/b404016c

upstream raw materials:

methyl 4-formylbenzoate

(5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one