ethanol; sodium hydride in diethyl ether Heating;

copper(II) sulfate in dichloromethane

sodium hydride in N,N-dimethyl-formamide

1: Et3N / 8 h / 50 - 60 °C 2: NaH / dimethylformamide View Scheme

T=175°C; further temperatures and catalysts;

(i) I2, Zn, Cu, Et2O, (ii) /BRN= 1747205/; Multistep reaction;

lithium aluminium tetrahydride in diethyl ether Reduction; 10 h; Heating;

diisobutylaluminium hydride in hexane; dichloromethane T=-78°C; 1 h;

(i) Zn, Cu, (ii) aq. NaOH; Multistep reaction;

1: 94 percent / K2CO3, H2O / methanol / 48 h / Ambient temperature 2: Et3N / tetrahydrofuran / 1 h / Ambient temperature 3: tetrahydrofuran / 3 h / Ambient temperature 4: 95 percent / 4 N H2SO4 / tetrahydrofuran / 4 h / Heating 5: 81 percent / LiAlH4 / diethyl ether 6: 1.) Et3N / 1.) CH2Cl2, 10 min, 2.) CH2Cl2, RT, 1 h 7: 62 percent / 15-crown-5 / dimethylsulfoxide / Ambient temperature 8: 83 percent / i-Bu2AlH / benzene; hexane / 3 h / 0 °C 9: 76 percent / CrO3, aq. H2SO4 / acetone / 0.5 h / Ambient temperature View Scheme