Multi-step reaction with 9 steps
1: Br2 / diethyl ether / 20 h / Ambient temperature
3: 2N HCl / methanol / 1 h / Heating
4: 1) NaCNBH3, 2N HCl / 1) MeOH, 2.5 h reflux, 2) CH2Cl2, 3 h, RT
5: 1) LDA / 1) THF, hexane, -15 deg C, 20 min, 2) THF, -15 deg C, 15 min
6: 96 percent / 48percent HBr / CH2Cl2 / 0.67 h
7: 90 percent / LiAlH4 / tetrahydrofuran / 0.5 h
8: 94 percent / CH2Cl2 / 1) 0 deg C, 2 h, 2) RT, 1 h
9: 93 percent / KOH / propan-2-ol / 1 h / Heating
With
hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; hydrogen bromide; bromine; sodium cyanoborohydride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; isopropyl alcohol;
DOI:10.1021/jo00055a023