(-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate

Base Information

• Chemical Name: (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate
• CAS No.: 1251618-11-7
• Molecular Formula: C₂₆H₃₁NO₃
• Molecular Weight: 405.537
• Mol file: 1251618-11-7.mol

Synonyms:(-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate

Chemical Property of (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate

There total 3 articles about (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate 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: 56.0%

(2S,3S)-3-phenyloxirane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester + benzonitrile (100-47-0) → (-)-menthyl (4R,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (1251618-10-6) + (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (1251618-11-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 4h; optical yield given as %de; Inert atmosphere;

Reference yield:

(-)-menthyl chloroacetate (7377-98-2,27994-88-3,88644-14-8,106916-72-7,111957-92-7,21758-29-2) → (-)-menthyl (4R,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (1251618-10-6) + (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (1251618-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide / tetrahydrofuran / 25 h / 20 °C

2: boron trifluoride diethyl etherate / dichloromethane / 4 h / -78 °C / Inert atmosphere

With boron trifluoride diethyl etherate; tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide; In tetrahydrofuran; dichloromethane; 1: Darzens condensation / 2: Ritter reaction;

Reference yield:

(-)-menthol (2216-51-5) → (-)-menthyl (4R,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (1251618-10-6) + (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (1251618-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 5.5 h / Reflux

2: tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide / tetrahydrofuran / 25 h / 20 °C

3: boron trifluoride diethyl etherate / dichloromethane / 4 h / -78 °C / Inert atmosphere

With boron trifluoride diethyl etherate; tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide; In tetrahydrofuran; dichloromethane; 2: Darzens condensation / 3: Ritter reaction;

upstream raw materials:

benzonitrile

(-)-menthol

(-)-menthyl chloroacetate

Downstream raw materials:

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid