methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate

Base Information

• Chemical Name: methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate
• CAS No.: 906450-06-4
• Molecular Formula: C₁₉H₂₄O₄
• Molecular Weight: 316.397
• Mol file: 906450-06-4.mol

Synonyms:methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate

Chemical Property of methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate

There total 1 articles about methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate 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: 57.0%

3-methoxyphenethyl iodide (25226-97-5) + methyl 2-methoxy-5-methylbenzoate (63113-79-1) → methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate (906450-06-4)

Guidance literature:

methyl 2-methoxy-5-methylbenzoate; With ammonia; lithium; In tetrahydrofuran; tert-butyl alcohol; at -78 - -33 ℃;

3-methoxyphenethyl iodide; In tetrahydrofuran; tert-butyl alcohol; at -78 - 20 ℃;

DOI:10.1021/ol061228f

Reference yield:

methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate (906450-06-4) → Benzoic acid 1-((4R,4aS,10aR)-10a-acetoxymethyl-7-methoxy-2-methyl-3,4,4a,9,10,10a-hexahydro-phenanthren-4-yl)-propyl ester

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / BF₃*Et₂O / CH₂Cl₂ / -24 - 20 °C

2: 75 percent / AlCl₃ / CH₂Cl₂ / 0.33 h / -78 °C

3: 74 percent / liq. ammonia; lithium / tetrahydrofuran / 0.25 h / -78 °C

4: Huenig's base; DMAP / CH₂Cl₂ / 0 - 20 °C

5: lithium aluminum hydride / diethyl ether / 0 - 20 °C

6: 4.2 g / pyridine; DMAP / 24 h / 20 °C

7: HCl

With pyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; aluminium trichloride; boron trifluoride diethyl etherate; ammonia; lithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ol061228f

Reference yield:

methyl 2-methoxy-1-(2'-(3''-methoxyphenyl)ethyl)-5-methylcyclohexa-2,5-diene-1-carboxylate (906450-06-4) → (2RS,4RS,4aSR,10aSR)-4-(1'-benzoyloxypropyl)-7-methoxy-2-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-1(2H)-one

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / BF₃*Et₂O / CH₂Cl₂ / -24 - 20 °C

2: 75 percent / AlCl₃ / CH₂Cl₂ / 0.33 h / -78 °C

3: 74 percent / liq. ammonia; lithium / tetrahydrofuran / 0.25 h / -78 °C

4: Huenig's base; DMAP / CH₂Cl₂ / 0 - 20 °C

5: lithium aluminum hydride / diethyl ether / 0 - 20 °C

6: 4.2 g / pyridine; DMAP / 24 h / 20 °C

7: HCl

8: 89 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

9: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / 0 °C

10: 70 percent / KOH / ethanol / 1 h

With pyridine; hydrogenchloride; dmap; potassium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; boron trifluoride diethyl etherate; ammonia; lithium; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ol061228f

upstream raw materials:

3-methoxyphenethyl iodide

methyl 2-methoxy-5-methylbenzoate