2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone

Base Information

• Chemical Name: 2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone
• CAS No.: 281661-49-2
• Molecular Formula: C₃₀H₄₀O₂Si
• Molecular Weight: 460.732
• Mol file: 281661-49-2.mol

Synonyms:2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone

Chemical Property of 2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone

There total 11 articles about 2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone 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: 73.0%

6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-2,2-dimethyl-4-oxo-oct-7-enal (281661-48-1) → 2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone (281661-49-2)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 80 ℃; for 72h;

DOI:10.1021/jo9918450

Reference yield:

3-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-pent-4-en-1-ol (281661-52-7) → 2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone (281661-49-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / 0.25 h / -60 - -50 °C

2.1: Mg / 0 °C

2.2: 83 percent / tetrahydrofuran / 1 h / 20 °C

3.1: 74 percent / PPTS / methanol / 8 h / 20 °C

4.1: 99 percent / oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / 0.25 h / -60 - -50 °C

5.1: 73 percent / NaOH / tetrahydrofuran; H₂O / 72 h / 80 °C

With sodium hydroxide; oxalyl dichloride; pyridinium p-toluenesulfonate; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Swern oxidation / 2.1: Solid phase reaction / 2.2: Grignard reaction / 3.1: desilylation / 4.1: Oxidation / 5.1: Cyclization;

DOI:10.1021/jo9918450

Reference yield:

3-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-pent-4-enoic acid methyl ester (281661-38-9) → 2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-allyl}-4,4-dimethyl-cyclopent-2-enone (281661-49-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

2.1: 89 percent / oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / 0.25 h / -60 - -50 °C

3.1: Mg / 0 °C

3.2: 83 percent / tetrahydrofuran / 1 h / 20 °C

4.1: 74 percent / PPTS / methanol / 8 h / 20 °C

5.1: 99 percent / oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / 0.25 h / -60 - -50 °C

6.1: 73 percent / NaOH / tetrahydrofuran; H₂O / 72 h / 80 °C

With sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; pyridinium p-toluenesulfonate; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1.1: Reduction / 2.1: Swern oxidation / 3.1: Solid phase reaction / 3.2: Grignard reaction / 4.1: desilylation / 5.1: Oxidation / 6.1: Cyclization;

DOI:10.1021/jo9918450

upstream raw materials:

6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-2,2-dimethyl-4-oxo-oct-7-enal

(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enal

3-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-pent-4-en-1-ol

3-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-pent-4-enoic acid methyl ester