Multi-step reaction with 10 steps
1: 99 percent / BH3SMe2 / tetrahydrofuran / 12 h / Ambient temperature
2: 91 percent / tetrahydrofuran / 5 h / 0 deg C to reflux
3: 97 percent / dimethylformamide; tetrahydrofuran / 6 h / 0 deg C to room temperature
4: 95 percent / NaCl, H2O / dimethylsulfoxide / 15 h / 180 °C
5: 73 percent / i-Bu2AlH / tetrahydrofuran / 2 h / -50 deg C to -30 deg C
6: 81 percent / PCC, Celite, Molecular Sieves / CH2Cl2 / 1 h / Ambient temperature
7: 1.) LDA / 1.) THF, -50 deg C, 30 min 2.) -78 deg C, 5 min
8: 98 percent / TEA / CH2Cl2 / 1.5 h / 0 deg C to room temperature
9: 100 percent / DBU / tetrahydrofuran / 2 h / Ambient temperature
10: 99 percent / LiOEt / tetrahydrofuran / 1 h / 25 °C
With
molecular sieve; dimethylsulfide borane complex; Celite; TEA; water; lithium ethoxide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; sodium chloride; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)95678-8