Technology Process of methyl-3-(4-methoxy-3-oxo-1-phenylsulfanyl-1,3,6,7,8,9-hexahydronaphtho[1,2-c]furan-1-yl)propionate
There total 6 articles about methyl-3-(4-methoxy-3-oxo-1-phenylsulfanyl-1,3,6,7,8,9-hexahydronaphtho[1,2-c]furan-1-yl)propionate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
4-methoxy-1-phenylsulfanyl-6,7,8,9-tetrahydro-1H-naphtho[1,2-c]furan-3-one;
With
lithium tert-butoxide;
In
tetrahydrofuran;
at -78 ℃;
for 0.5h;
Inert atmosphere;
poly(methacrylic acid);
In
tetrahydrofuran;
at -78 ℃;
Inert atmosphere;
Heating;
DOI:10.1021/jo301712b
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: potassium carbonate / acetone / 3 h / Reflux
2.1: potassium hydroxide; water / 0.5 h / Reflux
3.1: oxalyl dichloride / benzene; N,N-dimethyl-formamide / 2 h / 65 °C / Inert atmosphere
4.1: tetrahydrofuran / 0.25 h / 0 - 20 °C / Inert atmosphere
5.1: N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium / tetrahydrofuran / 0.75 h / -78 - 20 °C / Inert atmosphere
5.2: 12 h / 20 °C
6.1: acetic acid; hydrogenchloride; water / 10 h / Reflux
7.1: toluene-4-sulfonic acid / benzene / 10 h / Dean-Stark; Reflux
8.1: lithium tert-butoxide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
8.2: -78 °C / Inert atmosphere; Heating
With
hydrogenchloride; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; water; tert.-butyl lithium; potassium carbonate; toluene-4-sulfonic acid; acetic acid; potassium hydroxide; lithium tert-butoxide;
In
tetrahydrofuran; N,N-dimethyl-formamide; acetone; benzene;
8.1: |Hauser-Kraus Annulation / 8.2: |Hauser-Kraus Annulation;
DOI:10.1021/jo301712b
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 0.25 h / 0 - 20 °C / Inert atmosphere
2.1: N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium / tetrahydrofuran / 0.75 h / -78 - 20 °C / Inert atmosphere
2.2: 12 h / 20 °C
3.1: acetic acid; hydrogenchloride; water / 10 h / Reflux
4.1: toluene-4-sulfonic acid / benzene / 10 h / Dean-Stark; Reflux
5.1: lithium tert-butoxide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: -78 °C / Inert atmosphere; Heating
With
hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; water; tert.-butyl lithium; toluene-4-sulfonic acid; acetic acid; lithium tert-butoxide;
In
tetrahydrofuran; benzene;
5.1: |Hauser-Kraus Annulation / 5.2: |Hauser-Kraus Annulation;
DOI:10.1021/jo301712b
