(4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Base Information

• Chemical Name: (4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one
• CAS No.: 1446840-90-9
• Molecular Formula: C₂₄H₂₁FO₂
• Molecular Weight: 360.428

Synonyms:(4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Chemical Property of (4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Chemical Property:

Purity/Quality:

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Technology Process of (4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one

There total 4 articles about (4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one 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:

tert-butyl-(2-(1-chloro-3-(4-fluorophenyl)propyl)phenoxy)dimethylsilane (1446840-04-5) + 3-phenyl-propenal (104-55-2) → (4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-90-9) + (4R,5S)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one + (4R,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-94-3) + (4R,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Guidance literature:

With 18-crown-6 ether; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; tetrabutylammonium acetate; cesium fluoride; In tetrahydrofuran; at -18 ℃; for 12h; Inert atmosphere;

Reference yield:

(E)-3-phenylpropenal (14371-10-9) + tert-butyl-(2-(1-chloro-3-(4-fluorophenyl)propyl)phenoxy)dimethylsilane (1446840-04-5) → (4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-90-9) + (4R,5S)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one + (4R,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-94-3) + (4R,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Guidance literature:

With 18-crown-6 ether; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; tetrabutylammonium acetate; cesium fluoride; In tetrahydrofuran; at -18 ℃; for 12h; Overall yield = 85 %; Overall yield = 122 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja405833m

Reference yield:

2-((tert-butyldimethylsilyl)oxy)benzaldehyde (116585-12-7) → (4S,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-90-9) + (4R,5S)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one + (4R,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-94-3) + (4R,5R)-5-(4-fluorophenethyl)-4-phenyl-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether; tetrahydrofuran / 3 h / Inert atmosphere; Cooling with ice

2: thionyl chloride / toluene / 18 h / 0 - 20 °C / Inert atmosphere

3: tetrabutylammonium acetate; cesium fluoride; 18-crown-6 ether; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate / tetrahydrofuran / 12 h / -18 °C / Inert atmosphere

With thionyl chloride; 18-crown-6 ether; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; tetrabutylammonium acetate; cesium fluoride; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1021/ja405833m

upstream raw materials:

2-((tert-butyldimethylsilyl)oxy)benzaldehyde

(4-fluorophenylethyl)magnesium bromide

(E)-3-phenylpropenal

tert-butyl-(2-(1-chloro-3-(4-fluorophenyl)propyl)phenoxy)dimethylsilane

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