Technology Process of (S,E)-methyl 2-(4-(3-chlorobenzylidene)-1,3-dimethyl-5-oxocyclopent-2-enyl)acetate
There total 6 articles about (S,E)-methyl 2-(4-(3-chlorobenzylidene)-1,3-dimethyl-5-oxocyclopent-2-enyl)acetate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
(5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; sodium acetate; acetic acid;
In
diethyl ether;
at 22 ℃;
optical yield given as %ee;
enantioselective reaction;
Inert atmosphere;
Darkness;
DOI:10.1021/ol203375y
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: n-butyllithium / diethyl ether; hexane / 0.17 h / -78 °C
1.2: 2 h / -78 °C
1.3: 6 h / -80 - -40 °C / Inert atmosphere
2.1: hydrogenchloride; water / acetonitrile / 0.17 h / Cooling with ice
3.1: (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; sodium acetate; acetic acid / diethyl ether / 22 °C / Inert atmosphere; Darkness
With
hydrogenchloride; n-butyllithium; (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; water; sodium acetate; acetic acid;
In
diethyl ether; hexane; acetonitrile;
1.3: Liebeskind-modified Stille coupling / 3.1: Stetter cyclization;
DOI:10.1021/ol203375y
- Guidance literature:
-
Multi-step reaction with 2 steps
1: hydrogenchloride; water / acetonitrile / 0.17 h / Cooling with ice
2: (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; sodium acetate; acetic acid / diethyl ether / 22 °C / Inert atmosphere; Darkness
With
hydrogenchloride; (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; water; sodium acetate; acetic acid;
In
diethyl ether; acetonitrile;
2: Stetter cyclization;
DOI:10.1021/ol203375y
