methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate

Base Information

• Chemical Name: methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate
• CAS No.: 197726-05-9
• Molecular Formula: C₂₃H₃₀O₇
• Molecular Weight: 418.487
• Mol file: 197726-05-9.mol

Synonyms:methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate

Chemical Property of methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate

There total 10 articles about methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate 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:

3-(tert-Butyldimethylsiloxymethyl)benzyl Alcohol (81805-53-0) → methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate (197726-05-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 5 min

2: 1.) NaH / 1.) THF, 25 deg C, 30 min, 2.) THF, 25 deg C, 1 h

3: 1.) diisobutylaluminium hydride, 2.) MeOH, 3.) H₂O

4: 100 percent / DL-camphorsulfonic acid / CH₂Cl₂ / 1 h / 25 °C

5: 90 percent / aq. NaOH / ethanol / 2 h / Heating

6: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: 55 percent / dimethylsulfoxide / 1 h / 60 °C

8: aq. NaOH / ethanol / 10 h / Heating

9: diethyl ether; ethyl acetate

10: 1.) n-BuLi, diisopropylamine / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h

With methanol; sodium hydroxide; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; water; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; In diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0968-0896(97)00090-4

Reference yield:

3-(((tert-butyldimethylsilyl)oxy)methyl)benzaldehyde (81168-11-8) → methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate (197726-05-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) THF, 25 deg C, 30 min, 2.) THF, 25 deg C, 1 h

2: 1.) diisobutylaluminium hydride, 2.) MeOH, 3.) H₂O

3: 100 percent / DL-camphorsulfonic acid / CH₂Cl₂ / 1 h / 25 °C

4: 90 percent / aq. NaOH / ethanol / 2 h / Heating

5: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: 55 percent / dimethylsulfoxide / 1 h / 60 °C

7: aq. NaOH / ethanol / 10 h / Heating

8: diethyl ether; ethyl acetate

9: 1.) n-BuLi, diisopropylamine / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h

With methanol; sodium hydroxide; n-butyllithium; camphor-10-sulfonic acid; water; sodium hydride; diisobutylaluminium hydride; triethylamine; diisopropylamine; In diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0968-0896(97)00090-4

Reference yield:

3-(3-tetrahydropyranyloxy-1E-propenyl)benzylalcohol (197725-62-5) → methyl-6-methoxycarbonyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate (197726-05-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 55 percent / dimethylsulfoxide / 1 h / 60 °C

3: aq. NaOH / ethanol / 10 h / Heating

4: diethyl ether; ethyl acetate

5: 1.) n-BuLi, diisopropylamine / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h

With sodium hydroxide; n-butyllithium; triethylamine; diisopropylamine; In diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0968-0896(97)00090-4

upstream raw materials:

methyl 4-(chlorocarbonyl)butyrate

{3-[(E)-3-(Tetrahydro-pyran-2-yloxy)-propenyl]-phenyl}-acetic acid methyl ester

3-(tert-Butyldimethylsiloxymethyl)benzyl Alcohol

3-(((tert-butyldimethylsilyl)oxy)methyl)benzaldehyde

Downstream raw materials:

methyl-5-oxo-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate

methyl-5-acetoxy-6-[3-(2-formyl-E-ethenyl)phenyl]hexanoate

methyl 5-acetoxy-6-[3-(3-hydroxy-1E-propenyl)phenyl]hexanoate

methyl-5-hydroxy-6-[3-(3-tetrahydropyranyloxy-1E-propenyl)phenyl]hexanoate