2-Propenoic acid, (1S)-1-[2-[4-(phenylmethoxy)phenyl]ethyl]-3-butenyl ester

Base Information

• Chemical Name: 2-Propenoic acid, (1S)-1-[2-[4-(phenylmethoxy)phenyl]ethyl]-3-butenyl ester
• CAS No.: 850251-79-5
• Molecular Formula: C22H24O3
• Molecular Weight: 336.431
• Mol file: 850251-79-5.mol

Synonyms:

Chemical Property of 2-Propenoic acid, (1S)-1-[2-[4-(phenylmethoxy)phenyl]ethyl]-3-butenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Propenoic acid, (1S)-1-[2-[4-(phenylmethoxy)phenyl]ethyl]-3-butenyl ester

There total 10 articles about 2-Propenoic acid, (1S)-1-[2-[4-(phenylmethoxy)phenyl]ethyl]-3-butenyl 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: 90.0%

acryloyl chloride (814-68-6,25189-84-8) + (-)-(3S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol (767330-04-1) → (S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-yl acrylate (850251-79-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere; Cooling with ice;

DOI:10.14233/ajchem.2017.20816

Reference yield:

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → (S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-yl acrylate (850251-79-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 1.5 h / 20 °C / Inert atmosphere

4.1: Pseudomonas cepacia lipase / di-isopropyl ether / 24 h / 30 °C / Inert atmosphere; Enzymatic reaction

5.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere; Cooling with ice

With dmap; oxalyl dichloride; Pseudomonas cepacia lipase; potassium carbonate; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; dichloromethane; di-isopropyl ether; acetone; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 3.1: |Barbier Coupling Reaction / 3.2: |Barbier Coupling Reaction;

DOI:10.14233/ajchem.2017.20816

Reference yield:

benzyl bromide (100-39-0) → (S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-yl acrylate (850251-79-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 1.5 h / 20 °C / Inert atmosphere

4.1: Pseudomonas cepacia lipase / di-isopropyl ether / 24 h / 30 °C / Inert atmosphere; Enzymatic reaction

5.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere; Cooling with ice

With dmap; oxalyl dichloride; Pseudomonas cepacia lipase; potassium carbonate; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; dichloromethane; di-isopropyl ether; acetone; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 3.1: |Barbier Coupling Reaction / 3.2: |Barbier Coupling Reaction;

DOI:10.14233/ajchem.2017.20816

upstream raw materials:

acryloyl chloride

(-)-(3S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol

3-(4-(benzyloxy)phenyl)propanal

(+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol

Downstream raw materials:

(R)-6-(4-hydroxyphenethyl)tetrahydropyran-2-one

Centrolobin

(S)-6-[(4-benzyloxy)phenethyl]-5,6-dihydropyran-2-one