(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal

Base Information

• Chemical Name: (3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal
• CAS No.: 861118-37-8
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 861118-37-8.mol

Synonyms:(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal

Chemical Property of (3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal

There total 9 articles about (3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal 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: 98.0%

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-en-1-ol (861119-09-7) → (3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal (861118-37-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo0503862

Reference yield:

(3R)-3-(4-methoxybenzyloxy)-4,4-dimethyltetrahydrofuran-2-one → (3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal (861118-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran / 5 h / -78 - -35 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 - 0 °C / Inert atmosphere

2.2: 15 h / -78 - 20 °C / Inert atmosphere

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

With n-butyllithium; tetrapropylammonium perruthennate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexanes; dichloromethane; 2.2: Wittig reaction;

DOI:10.1016/j.tet.2011.03.113

Reference yield:

(2R)-(-)-3,3-dimethylbutane-1,2,4-triol (60856-63-5) → (3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal (861118-37-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 78 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 18 h / Heating

2.1: 89 percent / oxalyl chloride DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / 0 °C

3.2: 89 percent / tetrahydrofuran; hexane / 4 h / 0 °C

4.1: 97 percent / DIBAL-H / CH₂Cl₂ / -78 - 20 °C

5.1: 98 percent / oxalyl chloride DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation / 3.2: Wittig methylenation / 5.1: Swern oxidation;

DOI:10.1021/jo0503862

upstream raw materials:

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-en-1-ol

(2R)-(-)-3,3-dimethylbutane-1,2,4-triol

(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-carbaldehyde

(2R,4S)-2-(4-methoxyphenyl)-5,5-dimethyl-4-vinyl-1,3-dioxane

Downstream raw materials:

(2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol

(S)-6-(4-Methoxy-benzyloxy)-5,5-dimethyl-octa-1,7-dien-4-ol

(S)-6-(4-Methoxy-benzyloxy)-5,5-dimethyl-octa-1,7-dien-4-one

(3R,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol