Multi-step reaction with 10 steps
1: NaBH4 / ethanol; tetrahydrofuran / 1.5 h / 0 °C
2: CdCO3, HgCl2 / ethanol / 0.05 h / Heating
3: LiAlH4 / diethyl ether / 1.) 0 deg C, 20 min, 2.) room temp., 0.5 h
4: 80 percent / propanoic acid / 1 h / 140 - 150 °C
5: 94 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature
6: pyridine / 12 h / 0 - 4 °C
7: NaI / acetone / 4 h / Heating
8: 1.) K2CO3, 2.) p-TsOH / 1.) acetone, DMF, 70 deg C, 21 h, 2.) MeOH, 55 deg C, 30 min
9: 78 percent / 80percent m-chloroperoxybenzoic acid / CH2Cl2 / 4 h / Ambient temperature
10: LiAlH4 / diethyl ether / 2 h / Heating
With
pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; cadmium(II) carbonate; potassium carbonate; toluene-4-sulfonic acid; propionic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; mercury dichloride;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetone;