Technology Process of 1-acetoxy-3-[1-(tert-butyldimethylsilanyloxy)but-3-ynyl]-5-methylbenzene
There total 8 articles about 1-acetoxy-3-[1-(tert-butyldimethylsilanyloxy)but-3-ynyl]-5-methylbenzene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: HI / H2O / Heating
1.2: 2,6-lutidine
2.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C
2.2: 95 percent / tetrahydrofuran; pentane / 0.5 h / 0 °C
3.1: n-BuLi; TMEDA / diethyl ether; hexane; toluene / 0.03 h / -78 °C
3.2: 68 percent / various solvents / 1 h / -78 - 23 °C
4.1: 68 percent / imidazole; DMAP / CH2Cl2 / 16 h / 23 °C
5.1: TBAF; HOAc / tetrahydrofuran / 0 - 23 °C
6.1: 148 mg / pyridine / 16 h
With
pyridine; 1H-imidazole; dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; hydrogen iodide; tert.-butyl lithium; acetic acid;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; pentane;
DOI:10.1021/jo049426c
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 57 percent / sulfuric acid / 16 h
2.1: HI / H2O / Heating
2.2: 2,6-lutidine
3.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C
3.2: 95 percent / tetrahydrofuran; pentane / 0.5 h / 0 °C
4.1: n-BuLi; TMEDA / diethyl ether; hexane; toluene / 0.03 h / -78 °C
4.2: 68 percent / various solvents / 1 h / -78 - 23 °C
5.1: 68 percent / imidazole; DMAP / CH2Cl2 / 16 h / 23 °C
6.1: TBAF; HOAc / tetrahydrofuran / 0 - 23 °C
7.1: 148 mg / pyridine / 16 h
With
pyridine; 1H-imidazole; dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen iodide; tert.-butyl lithium; acetic acid;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; pentane;
DOI:10.1021/jo049426c
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 52 percent / Br2 / acetic acid
2.1: 57 percent / sulfuric acid / 16 h
3.1: HI / H2O / Heating
3.2: 2,6-lutidine
4.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C
4.2: 95 percent / tetrahydrofuran; pentane / 0.5 h / 0 °C
5.1: n-BuLi; TMEDA / diethyl ether; hexane; toluene / 0.03 h / -78 °C
5.2: 68 percent / various solvents / 1 h / -78 - 23 °C
6.1: 68 percent / imidazole; DMAP / CH2Cl2 / 16 h / 23 °C
7.1: TBAF; HOAc / tetrahydrofuran / 0 - 23 °C
8.1: 148 mg / pyridine / 16 h
With
pyridine; 1H-imidazole; dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen iodide; bromine; tert.-butyl lithium; acetic acid;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetic acid; toluene; pentane;
DOI:10.1021/jo049426c