(2S,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: (2S,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester
• CAS No.: 123078-43-3
• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.279
• Mol file: 123078-43-3.mol

Synonyms:

Chemical Property of (2S,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester

There total 2 articles about (2S,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester 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:

cyclopropyl phenyl ketone (3481-02-5) + chloroacetic acid ethyl ester (105-39-5) → (2R,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester (123078-43-3,123078-44-4) + (2S,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester (123078-43-3,123078-44-4)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; benzene; for 21h; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00282a020

Reference yield:

cyclopropyl phenyl ketone (3481-02-5) + chloroacetic acid ethyl ester (105-39-5) → (2R,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester (123078-43-3,123078-44-4) + (2S,3R)-3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester (123078-43-3,123078-44-4)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; benzene; for 21h; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00282a020

Reference yield:

3-Cyclopropyl-3-phenyl-oxirane-2-carboxylic acid ethyl ester (123078-43-3,123078-44-4) → 1-Methylnaphthalene (90-12-0,34475-76-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) potassium hydroxide, 2.) 1 N hydrochloric acid / 1.) ethanol, water, RT, 20 h

2: 50 percent / silver nitrate, sodium hydroxide / ethanol; H₂O / 24 h / Ambient temperature

3: oxalyl chloride / benzene / 3 h / Ambient temperature

4: pyridine / 3 h / 20 °C

5: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 15 min, 2.) from -30 deg C to 0 deg C

6: 99 percent / diisobutylaluminum hydride (Dibal-H) / CH₂Cl₂; hexane / 1 h / -10 °C

7: 89 percent / chromium trioxide, pyridine / CH₂Cl₂ / 1 h / 0 °C

8: 2.) water / 1.) ether, -78 deg C, 30 min, 2.) from -78 deg C to RT

9: 81 percent / chromium trioxide, pyridine / CH₂Cl₂ / 3 h / 0 °C

10: NaNH₂ / benzene / 12 h / Heating

With pyridine; chromium(VI) oxide; hydrogenchloride; potassium hydroxide; sodium hydroxide; oxalyl dichloride; water; diisobutylaluminium hydride; sodium amide; silver nitrate; lithium diisopropyl amide; In ethanol; hexane; dichloromethane; water; benzene;

DOI:10.1021/jo00282a020

upstream raw materials:

cyclopropyl phenyl ketone

chloroacetic acid ethyl ester

Downstream raw materials:

2-cyclopropyl-2-phenylacetaldehyde

methyl 2-cyclopropyl-2-phenylacetate

2-cyclopropyl(phenyl)ethanoic acid

2-cyclopropyl-2-phenylpropionic acid