406945-07-1

Basic information

• Product Name: (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether
• Synonyms: (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether
• CAS NO: 406945-07-1
• Molecular Weight: 332.322
• Mol File: 406945-07-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether(406945-07-1)
• EPA Substance Registry System: (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether(406945-07-1)

Safety Data

• Hazardous Substances Data: 406945-07-1(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 498-60-2 furan-3-carboxaldehyde 
• 98-08-8 α,α,α-trifluorotoluene 
• 184844-76-6 (S)-2-(3-furyl)-1-phenyl-1-ethanol 

Downstream Products

• 406945-09-3 (S)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propanamide 
• 114247-06-2 (S)-fluoxetine hydrochloride 
• 100568-02-3 (S)-fluoxetine 
• 406945-08-2 (S)-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propionic acid 

Relevant articles and documents

Enantioselective synthesis of (S)- and (R)-fluoxetine hydrochloride

The enantioselective synthesis of fluoxetine hydrochloride, a potent serotonin-uptake inhibitor, is described. The synthesis of (S)-fluoxetine hydrochloride begins with the asymmetric carbonyl-ene reaction of benzaldehyde with 3-methylene-2,3-dihydrofuran (1) catalyzed by Ti[OCH(CH3)2]4/(S)-BINOL to give (S)-2-(3-furyl)-1-phenyl-1-ethanol (2) in 90% yield and 95% ee. In five steps, alcohol 2 was converted into (S)-fluoxetine hydrochloride (97% ee and 56% overall yield from benzaldehyde). (R)-fluoxetine hydrochloride was prepared by the same sequence except that Ti[OCH(CH3)2]4/(R)-BINOL was used in the first reaction to give the enantiomer of 2.