rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate

Base Information

• Chemical Name: rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate
• CAS No.: 139622-44-9
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Mol file: 139622-44-9.mol

Synonyms:rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate

Chemical Property of rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate

There total 3 articles about rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate 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: 72.0%

(+/-) methyl (4,5)-trans-epoxy-(2E)-hexenoate (14202-27-8,51830-12-7,67315-16-6,70095-87-3,70494-79-0,139686-29-6,139686-31-0,139686-32-1) + methoxybenzene (100-66-3) → rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate (139622-44-9)

Guidance literature:

With boron trifluoride diethyl etherate;

DOI:10.1016/j.tetasy.2009.04.015

Reference yield: 53.0%

(+/-) methyl (4,5)-trans-epoxy-(2E)-hexenoate (14202-27-8,51830-12-7,67315-16-6,70095-87-3,70494-79-0,139686-29-6,139686-31-0,139686-32-1) + methoxybenzene (100-66-3) → rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate (139622-44-9) + methyl (4,5)-anti-4-(2'-methoxyphenyl)-5-hydroxy-2(E)-hexenoate

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - -20 ℃; for 2h;

DOI:10.1248/cpb.53.1259

Reference yield:

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → rac-(2E,4S,5S)-methyl 5-hydroxy-4-(4-methoxyphenyl)-hex-2-enoate (139622-44-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / MCPBA / CH₂Cl₂ / 24 h / Ambient temperature

2: 33 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1248/cpb.41.55

upstream raw materials:

(+/-) methyl (4,5)-trans-epoxy-(2E)-hexenoate

methoxybenzene

(2E,4E)-methylhexa-2,4-dienoate

Downstream raw materials:

(2E,4R,5R)-methyl 5-acetoxy-4-(4-methoxyphenyl)hex-2-enoate