Multi-step reaction with 15 steps
1: 1.) LDA / 1.) THF, -78 deg C, 1.5 h, 2.) -78 deg C, 45 min
2: N-bromosuccinimide, AIBN / CCl4 / 0.33 h / Heating
3: calcium carbonate / dimethylformamide / 4 h / 90 °C
4: 1.) NaH / 1.) THF, reflux, 1.5 h, 2.) reflux, 16 h
5: 98 percent / aq. HF / acetonitrile / 1 h / Ambient temperature
6: tri-n-butyl phosphine / tetrahydrofuran / 0.75 h
7: 30percent aq. hydrogen peroxide / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 3 h
8: 88 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 1 h, 2.) 25 deg C, 1 h
9: 78 percent / oxalyl chloride, DMSO, triethylamine / CH2Cl2 / -78 - 20 °C
10: Eu(fod)3, molecular sives (4 Angstroem) / CH2Cl2 / 120 h / Ambient temperature
11: 52 percent / diazabicyclo<5.4.0>undec-7-ene / benzene / 12 h
12: 98 percent / LiAlH4 / diethyl ether / 2 h / 0 °C
13: 4-dimethylaminopyridine, Et3N / CH2Cl2 / 36 h / Ambient temperature
14: 92 percent / diisopropylethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 4 h / Ambient temperature
15: 1.) O2, tetraphenylporphine, 2.) LiAlH4 / 1.) CS2, -78 deg C, 5 h, irradiation, 2.) ether, -78 deg C, 1.5 h
With
dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; molecular sives (4 Angstroem); hydrogen fluoride; dihydrogen peroxide; oxygen; 5,15,10,20-tetraphenylporphyrin; sodium hydride; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; calcium carbonate; lithium diisopropyl amide; Eu(fod)3;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
