Technology Process of (2Z)-2-[(4S)-4-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]ethanol
There total 6 articles about (2Z)-2-[(4S)-4-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]ethanol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
tetrakis(triphenylphosphine) palladium(0); triethylamine;
In
acetonitrile;
for 4h;
Heating;
DOI:10.1021/jo050568w
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: (COCl)2; DMSO; Et3N
2.1: (R)-(+)-1,1'-bi-2-naphthol; Ti(Oi-Pr)4; molecular sieves 4 Angstroem / CH2Cl2 / 0.17 h / 20 °C
2.2: 1.2 g / CH2Cl2 / 72 h / -18 °C
3.1: 92 percent / imidazole / dimethylformamide / 15 h / 20 °C
4.1: nBuLi / hexane; tetrahydrofuran / 1 h / -30 °C
4.2: 91 percent / tetrahydrofuran; hexane / -30 - 20 °C
5.1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene; diethyl ether / 8.17 h / -5 - 25 °C
5.2: 70 percent / I2 / tetrahydrofuran; diethyl ether; toluene / 4 h / -78 °C
6.1: 85 percent / Et3N; (PhP)4Pd / acetonitrile / 4 h / Heating
With
1H-imidazole; titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; oxalyl dichloride; 4 A molecular sieve; (R)-1,1'-Bi-2-naphthol; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
1.1: Swern oxidation / 6.1: Heck cyclization;
DOI:10.1021/jo050568w
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: (R)-(+)-1,1'-bi-2-naphthol; Ti(Oi-Pr)4; molecular sieves 4 Angstroem / CH2Cl2 / 0.17 h / 20 °C
1.2: 1.2 g / CH2Cl2 / 72 h / -18 °C
2.1: 92 percent / imidazole / dimethylformamide / 15 h / 20 °C
3.1: nBuLi / hexane; tetrahydrofuran / 1 h / -30 °C
3.2: 91 percent / tetrahydrofuran; hexane / -30 - 20 °C
4.1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene; diethyl ether / 8.17 h / -5 - 25 °C
4.2: 70 percent / I2 / tetrahydrofuran; diethyl ether; toluene / 4 h / -78 °C
5.1: 85 percent / Et3N; (PhP)4Pd / acetonitrile / 4 h / Heating
With
1H-imidazole; titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; 4 A molecular sieve; (R)-1,1'-Bi-2-naphthol; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
5.1: Heck cyclization;
DOI:10.1021/jo050568w
