racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate

Base Information

• Chemical Name: racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate
• CAS No.: 17071-33-9
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 17071-33-9.mol

Synonyms:racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate

Chemical Property of racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate

There total 9 articles about racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate 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: 98.0%

ethyl acetoacetate (141-97-9) + benzaldehyde (100-52-7) → racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate (17071-33-9)

Guidance literature:

ethyl acetoacetate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -50 ℃; for 1h;

benzaldehyde; In tetrahydrofuran; hexane; at -50 ℃; for 3h; regioselective reaction;

DOI:10.1071/CH12062

Reference yield: 90.0%

bromo(2-ethoxy-2-oxoethyl)zinc (5764-82-9) + benzaldehyde (100-52-7) → racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate (17071-33-9)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at 50 ℃; Temperature; Time; Inert atmosphere;

DOI:10.1021/jo400408t

Reference yield:

5-(2-Chloro-acetoxy)-3-oxo-5-phenyl-pentanoic acid ethyl ester (848900-76-5) → racemic ethyl 5-hydroxy-3-oxo-5-phenylpentanoate (17071-33-9) + ethyl 3-oxo-5-phenyl-4-pentenoate (1503-99-7,58369-48-5)

Guidance literature:

With ammonium hydroxide; In methanol; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2004.12.059

upstream raw materials:

4-methyleneoxetan-2-one

ethanol

benzaldehyde

ethyl acetoacetate

Downstream raw materials:

ethyl syn-3,5-dihydroxy-5-phenylvalerate

(3RS,5SR)-3,5-dihydroxy-5-phenyl-pentanoic acid ethyl ester

ethyl (3R,5S)-3,5-dihydroxy-5-phenylpentanoate

ethyl 3-oxo-5-phenylpentanoate