Multi-step reaction with 16 steps
1: 5.50 g / Cl2 / CH2Cl2; CCl4 / 1) -78 deg C, 40 min, 2) 0 deg C, 20 min
2: 3.35 g / Ag2O, AgBF4 / tetrahydrofuran / 1) -30 deg C, 2) -15 deg C, 2.5h, 3) room temperature, 1h
3: 36 percent / K2CO3 / acetone; H2O / 3 h / 55 °C
4: 68 percent / Pyridine / CH2Cl2 / 1) -35 deg C -> 0 deg C, 1h, 2) 0 deg C, 1h
5: 0.880 g / Pyridine / tetrahydrofuran / 1.5 h / -78 deg C -> room temp.
6: 0.730 g / camphorsulfonic acid, H2O / CH2Cl2 / 0.58 h / Ambient temperature
7: 80 percent / O3 / ethyl acetate / -78 °C
8: 1.49 g / Zn dust, propionic acid / CH2Cl2 / 0.5 h / 1) 0 deg C -> 13 deg C, 30 min, 2) 0 deg C after 30 min
9: 1.31 g / 2,6-Lutidine, SOCl2 / CH2Cl2 / 1) -30 deg C -> 0 deg C , 20 min, 2) 0 deg C, 1.5h
10: 0.99 g / CH2Cl2 / 1) 12 h, room temperature, 2) 4.5 h heating
11: 75 percent / Zn dust, acetic acid / CH2Cl2 / 5 h / 15 °C
12: 85 percent / acetic anhydride / dimethylsulfoxide / 4 h / Ambient temperature
14: 1) DMF, POCl3, 2) Pyridine
15: 0.102 g / Zn dust, AcOH / CH2Cl2 / 0.33 h / Ambient temperature
16: 0.125 g / H2 / palladium black / ethyl acetate; ethanol / 0.25 h
With
pyridine; 2,6-dimethylpyridine; silver tetrafluoroborate; thionyl chloride; camphor-10-sulfonic acid; water; hydrogen; acetic anhydride; chlorine; potassium carbonate; ozone; acetic acid; propionic acid; N,N-dimethyl-formamide; silver(l) oxide; zinc; trichlorophosphate;
palladium;
In
tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone;
DOI:10.1021/jo01306a028