1.1: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere 1.2: 0.67 h / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere 3.2: 18 h / -78 - 20 °C / Inert atmosphere 4.1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere 5.1: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere 6.1: copper(I) thiophene-2-carboxylate; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl / tetrahydrofuran / -78 °C / Inert atmosphere 7.1: sodium tetrahydroborate; water / Inert atmosphere View Scheme

1: 1-bromo-3-(propan-2-yl)benzene With n-butyllithium in tetrahydrofuran T=-60°C; 0.5 h; 2: N,O-dimethylacetohydroxamic acid in tetrahydrofuran T=-30°C; 3 h;

pyridine T=150°C; 13 h;

tetrakis(triphenylphosphine) palladium(0) in 1-methyl-pyrrolidin-2-one T=125°C; 2.5 h;

pyridine T=190°C;

1: (i) Mg, (ii) /BRN= 505984/, (iii) KHSO4 2: aq. NaOH, <PhCH2NEt3>Cl 3: NaOMe / diethyl ether View Scheme

1: 1-bromo-3-(propan-2-yl)benzene With magnesium; ethylene dibromide in tetrahydrofuran 0.5 h; Inert atmosphereReflux; 2: formaldehyd in tetrahydrofuran 1 h; Inert atmosphere;

1.1: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere 1.2: 0.67 h / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme