Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester

Base Information

• Chemical Name: Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester
• CAS No.: 97580-38-6
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• Mol file: 97580-38-6.mol

Synonyms:Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester

Chemical Property of Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester

There total 6 articles about Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic 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: 61.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + {2-[1-(4-Methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester (97580-35-3) → Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester (97580-38-6)

Guidance literature:

With caesium carbonate; In tetrahydrofuran; for 15h; Ambient temperature;

DOI:10.1021/jo00354a035

Reference yield:

(E)-ethyl 3-(4-methoxyphenyl)but-2-enoate (7706-82-3) → Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester (97580-38-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, diisopropylamine / 1.) hexane, THF, -78 deg C, 0.5 h, 2.) hexane, THF, RT, 1 h

2: 81.6 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

3: 82 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

4: hydrazine hydrate / ethanol / 3 h / Heating

5: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

6: 61 percent / Cs₂CO₃ / tetrahydrofuran / 15 h / Ambient temperature

With lithium aluminium tetrahydride; n-butyllithium; di-isopropyl azodicarboxylate; caesium carbonate; hydrazine hydrate; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00354a035

Reference yield:

2-(1-4'-methoxyphenylethenyl)-5-hexen-1-ol (97580-26-2) → Hydroxymethyl-{2-[1-(4-methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester (97580-38-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

2: hydrazine hydrate / ethanol / 3 h / Heating

3: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

4: 61 percent / Cs₂CO₃ / tetrahydrofuran / 15 h / Ambient temperature

With di-isopropyl azodicarboxylate; caesium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo00354a035

upstream raw materials:

formaldehyd

{2-[1-(4-Methoxy-phenyl)-vinyl]-hex-5-enyl}-carbamic acid methyl ester

(E)-ethyl 3-(4-methoxyphenyl)but-2-enoate

2-(1-4'-methoxyphenylethenyl)-5-hexen-1-ol

Downstream raw materials:

(4aS,6R,8aR)-6-Formyloxy-4a-(4-methoxy-phenyl)-octahydro-isoquinoline-2-carboxylic acid methyl ester

(4aR,6S,8aS)-4a-(4-Methoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester

(4aS,6S,8aS)-4a-(4-Methoxy-phenyl)-2-methyl-decahydro-isoquinolin-6-ol

(4aS,6R,8aR)-4a-(4-Methoxy-phenyl)-2-methyl-decahydro-isoquinolin-6-ol