(S)-8-(benzyloxy)-6-bromo-7-methyl-1,4-dioxaspiro[4.4]non-6-ene

Base Information

• Chemical Name: (S)-8-(benzyloxy)-6-bromo-7-methyl-1,4-dioxaspiro[4.4]non-6-ene
• CAS No.: 1319079-39-4
• Molecular Formula: C₁₅H₁₇BrO₃
• Molecular Weight: 325.202
• Mol file: 1319079-39-4.mol

Synonyms:

Chemical Property of (S)-8-(benzyloxy)-6-bromo-7-methyl-1,4-dioxaspiro[4.4]non-6-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-8-(benzyloxy)-6-bromo-7-methyl-1,4-dioxaspiro[4.4]non-6-ene

There total 5 articles about (S)-8-(benzyloxy)-6-bromo-7-methyl-1,4-dioxaspiro[4.4]non-6-ene 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:

(S)-9-bromo-8-methyl-1,4-dioxaspiro[4.4]non-8-en-7-ol (1319079-22-5) + benzyl bromide (100-39-0) → (S)-8-(benzyloxy)-6-bromo-7-methyl-1,4-dioxaspiro[4.4]non-6-ene (1319079-39-4)

Guidance literature:

(S)-9-bromo-8-methyl-1,4-dioxaspiro[4.4]non-8-en-7-ol; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

benzyl bromide; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo201020v

Reference yield:

6-bromo-7-methyl-1,4-dioxaspiro<4.4>non-6-ene (70156-97-7) → (S)-8-(benzyloxy)-6-bromo-7-methyl-1,4-dioxaspiro[4.4]non-6-ene (1319079-39-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tert.-butylhydroperoxide; sodium chlorite / water; acetonitrile / 17 h / 50 °C / Inert atmosphere; Molecular sieve

2.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 5 h / 0 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

With tert.-butylhydroperoxide; sodium chlorite; dimethylsulfide borane complex; sodium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; water; acetonitrile;

DOI:10.1021/jo201020v

Reference yield:

2-bromo-3-methyl-2-cyclopentene-1-one (80963-36-6) → (S)-8-(benzyloxy)-6-bromo-7-methyl-1,4-dioxaspiro[4.4]non-6-ene (1319079-39-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / orthoformic acid triethyl ester / 20 °C / Inert atmosphere

2.1: tert.-butylhydroperoxide; sodium chlorite / water; acetonitrile / 17 h / 50 °C / Inert atmosphere; Molecular sieve

3.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 5 h / 0 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

With tert.-butylhydroperoxide; sodium chlorite; dimethylsulfide borane complex; sodium hydride; toluene-4-sulfonic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; water; orthoformic acid triethyl ester; acetonitrile;

DOI:10.1021/jo201020v

upstream raw materials:

3-Methyl-2-cyclopenten-1-one

9-bromo-8-methyl-1,4-dioxaspiro[4.4]non-8-en-7-one

(S)-9-bromo-8-methyl-1,4-dioxaspiro[4.4]non-8-en-7-ol

benzyl bromide

Downstream raw materials:

(1S,4S)-4-(benzyloxy)-2-bromo-3-methyl-1-(prop-1-en-2-yl)cyclopent-2-enol

(S)-4-(benzyloxy)-2-bromo-3-methylcyclopent-2-enone

4-(benzyloxy)-2-bromo-1-isopropyl-3-methylcyclopent-2-enol

(1S,4S)-4-(benzyloxy)-2-bromo-1-isopropyl-3-methylcyclopent-2-enol