toluene-4-sulfonic acid in benzene 65 h; Heating;

1: dimethyl lt;1-(methoxycarbonyl)ethylgt;phosphonate With sodium hydride in tetrahydrofuran; mineral oil T=0 - 40°C; Horner-Wadsworth-Emmons olefination; 2: pentanal in tetrahydrofuran; mineral oil Horner-Wadsworth-Emmons olefination; 24 h; Reflux; 3: With platinum(IV) oxide; hydrogen in methanol

1: 100 percent / chlorotrimethylsilane / methanol / 3 h / Ambient temperature 2: 60 °C View Scheme

1: aqu. KOH / ethanol / 5 h / Heating 2: 1.) 30 min, 150 deg; 2.) in 15 min to 180 deg C 3: H2SO4 / 1 h / Heating View Scheme

T=60°C;

1: 1.) 30 min, 150 deg; 2.) in 15 min to 180 deg C 2: H2SO4 / 1 h / Heating View Scheme

bis-triphenylphosphine-palladium(II) chloride T=110°C; P=15001.2 Torr; 4 h; effect of solvent, effect of CoCl2 additive; Product distribution;

1: 1.) LiAlH4; 2.) HCl / 1.) diethyl ether, 8 h, reflux; 2.) 0 deg C, water 2: pyridine / 1 h / 0 °C 3: LiBr / acetone / 5 h / Heating View Scheme