trans-2,3-bis(3-methoxybenzyl)-4-butanolide

Base Information

• Chemical Name: trans-2,3-bis(3-methoxybenzyl)-4-butanolide
• CAS No.: 77756-17-3
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.392
• Mol file: 77756-17-3.mol

Synonyms:

Chemical Property of trans-2,3-bis(3-methoxybenzyl)-4-butanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-2,3-bis(3-methoxybenzyl)-4-butanolide

There total 30 articles about trans-2,3-bis(3-methoxybenzyl)-4-butanolide 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: 80.0%

3-Hydroxymethyl-2-(4-methoxy-benzyl)-4-(3-methoxy-phenyl)-N,N-dimethyl-butyramide → trans-2,3-bis(3-methoxybenzyl)-4-butanolide (77756-17-3,77786-23-3,78473-70-8,80704-91-2,93578-50-8)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 4h; Heating;

DOI:10.1016/S0040-4039(00)88673-6

Reference yield: 18.0%

4-<(3-methoxyphenyl)methyl>dihydrofuran-2(3H)-one (86653-16-9) + 1-bromomethyl-3-methoxybenzene (874-98-6) → trans-2,3-bis(3-methoxybenzyl)-4-butanolide (77756-17-3,77786-23-3,78473-70-8,80704-91-2,93578-50-8)

Guidance literature:

4-<(3-methoxyphenyl)methyl>dihydrofuran-2(3H)-one; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; at -78 ℃;

1-bromomethyl-3-methoxybenzene; at -78 ℃; Further stages.;

DOI:10.1039/b008499i

Reference yield:

1-bromomethyl-3-methoxybenzene (874-98-6) → trans-2,3-bis(3-methoxybenzyl)-4-butanolide (77756-17-3,77786-23-3,78473-70-8,80704-91-2,93578-50-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Bu₃SnH / Pd(PPh₃)4

1.2: NMO; TPAP / 62 h / -78 - 23 °C

1.3: Pd₂(dba)3

2.1: 92 percent / H₂ / 10percent Pd/C / 14 h / 75007.5 Torr

3.1: LDA; DMPU / -78 °C

3.2: 18 percent / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hydrogen; tri-n-butyl-tin hydride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1.3: Stille coupling reaction;

DOI:10.1039/b008499i

upstream raw materials:

trans-2,3-bis(3-methoxybenzyl)-4-butanolide

bis(3-methoxybenzylidene)succinic acid

3-methoxy-benzaldehyde

[(3-methoxyphenyl)methyl]propanedioic acid diethyl ester

Downstream raw materials:

(3S,4R)-3,4-Bis-(3-hydroxy-benzyl)-dihydro-furan-2-one

trans-2,3-bis[(3-hydroxyphenyl)methyl]-γ-butyrolactone

2,3-bis(3-methoxybenzyl)-4-butanolide

trans-3,4-bis(3-methoxybenzyl)tetrahydrofuran

Refernces

• 1、 Doyle, Michael P.,Protopopova, Marina N.,Zhou, Qi-Lin,Bode, Jeffrey W.,Simonsen, Stanley H.,Lynch, Vincent. "Optimization of Enantiocontrol for Carbon-Hydrogen Insertion with Chiral Dirhodium(II) Carboxamidates. Synthesis of Natural Dibenzylbutyrolactone Lignans from 3-Aryl-1-propyl Diazoacetates in High Optical Purity". . p. 6654 - 6655. Retrieved 2007/10/03.
• 2、 Bambagiotti-Alberti, Massimo,Coran, Silvia A.,Vincieri, Franco F.,Nostro, Pierandrea Lo. "CONVENIENT RUTHENIUM-COMPLEX CATALYSED SYNTHESIS OF ENTEROLACTONE FROM THE CORRESPONDING DIBENZYLIDENE SUCCINIC ACID MOIETY". . p. 1735 - 1738. Retrieved 2007/10/02.