Multi-step reaction with 20 steps
1: 99 percent / LiAlH4 / diethyl ether / 0.33 h / -5 °C
2: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature
3: 100 percent / NEt3, DMAP / CH2Cl2 / 15 h / Ambient temperature
4: 1) (COCl)2, DMSO, 2) NEt3 / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, 0 deg C, 10 min
5: 99 percent / LiAlH4 / diethyl ether / 0.25 h / -20 °C
6: 97 percent / 2,6-lutidine / CH2Cl2 / 1 h / Ambient temperature
7: 100 percent / DDQ / CH2Cl2; H2O / 0.67 h / Ambient temperature
8: 44 percent / H2 / Pd(OH)2-C / ethanol; ethyl acetate / 168 h / 760 Torr / Ambient temperature
9: 96 percent / p-TsOH*H2O / 0.5 h / Ambient temperature
10: 99 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 31 h / Ambient temperature
11: 94 percent / p-TsOH*H2O / methanol / 0.83 h / Ambient temperature
12: 83 percent / NEt3, DMAP / CH2Cl2 / 3 h / Ambient temperature
13: 86 percent / NaI / acetone / 8 h / 50 °C
14: 98 percent / NEt3 / CH2Cl2 / 0.17 h / -10 °C
15: 98 percent / acetonitrile / 27 h / 60 °C
16: 1) NaHMDS / 1) THF, room temperature, 1 h, 2) THF, room temperature, 30 min
17: 96 percent / K2CO3 / methanol / 1.5 h / 0 °C
18: 38 percent / tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium / toluene / 21 h / 80 °C
19: 60 percent / DMAP, pyridine / CH2Cl2 / 0.33 h / Ambient temperature
20: 1) NaBH4 / 1) EtOH, 0 deg C, 5 min, 0 deg C -> room temperature, 30 min, 2) EtOH, reflux, 50 min
With
pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide;
palladium hydroxide - carbon;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(97)10254-X