methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate

Base Information

• Chemical Name: methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate
• CAS No.: 887259-43-0
• Molecular Formula: C₂₇H₂₂O₇
• Molecular Weight: 458.467
• Mol file: 887259-43-0.mol

Synonyms:methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate

Chemical Property of methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate

There total 7 articles about methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate 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: 38.0%

5-(4-benzyloxy)-6-(benzyloxymethylene)-5-(4-benzyloxyphenyl)-2,2,8,8-tetramethyl-3,7-dioxa-2,8-disilanon-4-ene (887259-41-8) + oxalyl dichloride (79-37-8) → methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate (887259-43-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1002/ejoc.200500837

Reference yield:

methyl 4-benzyloxy-2-[4-(benzyloxy)phenyl]-3-oxobutanoate (887259-39-4) → methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate (887259-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / tetrahydrofuran / 12 h / 20 °C

1.2: 100 percent / lithium diisopropylamide / tetrahydrofuran / -78 - 20 °C

2.1: 38 percent / trimethylsilyl triflate / CH₂Cl₂ / -78 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.200500837

Reference yield:

4-hydroxyphenylacetate (156-38-7) → methyl [3-(benzyloxy)-4-hydroxy-5-oxofuran-2(5H)-ylidene](4-benzyloxyphenyl)acetate (887259-43-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / BF₃*Et₂O / 11 h / 20 °C

2.1: 91 percent / potassium carbonate / acetone / 18 h / Heating

3.1: 49 percent / lithium diisopropylamide; HMPA / tetrahydrofuran / -78 - 20 °C

4.1: Et₃N / tetrahydrofuran / 12 h / 20 °C

4.2: 100 percent / lithium diisopropylamide / tetrahydrofuran / -78 - 20 °C

5.1: 38 percent / trimethylsilyl triflate / CH₂Cl₂ / -78 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; potassium carbonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetone; 3.1: Claisen condensation;

DOI:10.1002/ejoc.200500837

upstream raw materials:

5-(4-benzyloxy)-6-(benzyloxymethylene)-5-(4-benzyloxyphenyl)-2,2,8,8-tetramethyl-3,7-dioxa-2,8-disilanon-4-ene

oxalyl dichloride

methyl 4-benzyloxy-2-[4-(benzyloxy)phenyl]-3-oxobutanoate

4-hydroxyphenylacetate

Downstream raw materials:

methyl {3-benzyloxy-5-oxo-4-[(trifluoromethylsulfonyl)oxy]furan-2(5H)-ylidene}(4-benzyloxyphenyl)acetate