water; triphenylmethane tetrafluoroborate in acetonitrile Ambient temperature; Product distribution;

1: benzyl 5-methoxycarbonylpentyl ether With diisobutylaluminium hydride in tetrahydrofuran T=0°C; 2 h; 2: p-toluenesulfonyl chloride With pyridine in dichloromethane

1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / 0 °C 2: cesium fluoride / N,N-dimethyl-formamide / 10 h / 50 °C 3: hydrogen; palladium 10 on activated carbon / methanol / 2 h / 760.05 Torr / |Inert atmosphere View Scheme