lithium aluminium tetrahydride in tetrahydrofuran

1: 66 percent 2: 41 percent / LiAlH4 / tetrahydrofuran View Scheme

lithium aluminium tetrahydride in diethyl ether Heating;

sodium azide; sulfuric acid; benzene

sodium tetrahydroborate; tin(IV) chloride

diethyl ether; phenyllithium; diethylamine

1: H2SO4; AcOH / ethanol / 20 °C 2: HCl / ethanol / Heating View Scheme

1: 96 percent / Et3N / tetrahydrofuran / 14.5 h / 0 - 20 °C 2: 67 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

2: LiAlH4; diethyl ether 3: phenyl lithium; diethyl ether; diethylamine View Scheme

1: 2-(3-chloro-phenyl)-ethylamine; 4-formyl-3,5-dimethoxyphenoxy-Merrifield resin With sodium tris(acetoxy)borohydride in acetic acid; N,N-dimethyl-formamide T=20°C; Solid phase reaction; reductive amination; 69 h; 2: chloroacetic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide in N,N-dimethyl-formamide T=20°C; Solid phase reaction; acylation; 15 h; 3: With dimethylsulfide; water; trifluoroacetic acid in dichloromethane T=20°C; Solid phase reaction; cleavage of amide; 15 h;