1: 1.) Merrifield resin, Na; 2.) aq. Na2CO3; 3.) aq. HCl / 2.) Pd(PPh3)4 / 2.) DME, reflux, 48 h; 3.) dioxan, 80 deg C, 48 h 2: LiAlH4 3: CrO3 in H2SO4 / acetone View Scheme

1: 1.) Merrifield resin, Na; 2.) aq. Na2CO3; 3.) aq. HCl / 2.) Pd(PPh3)4 / 2.) DME, reflux, 48 h; 3.) dioxan, 80 deg C, 48 h 2: LiAlH4 View Scheme

Multi-step reaction with 2 steps 1.1: 89 percent / pyridine / 6 h / 110 °C2.1: sec-butyllithium; TMEDA / tetrahydrofuran / -78 - 20 °C2.2: 82 percent / trimethylborate / tetrahydrofuran / 3 h / -78 °C