1: 1-bromo-3-methyl-butane With magnesium 2: acrylic acid methyl ester With 4-(N,N-dimethlyamino)pyridine; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex in tetrahydrofuran T=-78°C; 3.5 h;

1: water; alcohol / die Loesung giesst man vom ausgeschiedenen Kaliumbromid ab, kocht sie mit Kaliumhydroxyd und dampft nach der Zugabe von Wasser zur Entfernung des Alkohols ein;man saeuert die Loesung mit verd.Schwefelsaeure an 2: potassium permanganate View Scheme

ethanol

sodium hydroxide; Aliquatreg; 336 1) H2O-C6H6, room temperature, 2 h, 2) room temperature, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

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1.1: magnesium / diethyl ether 1.2: 98 percent / CuI / diethyl ether / 12 h / -78 - -20 °C 2.1: 96 percent / KOH / diethyl ether / 6 h / 0 - 20 °C 3.1: 95 percent / CuI / tetrahydrofuran / 12 h / -78 °C 4.1: NaH / dimethylformamide / 0.5 h / 20 °C 4.2: 97 percent / tetra-n-butylammonium iodide / dimethylformamide / 1 h / 0 °C 5.1: BH3*DMS / tetrahydrofuran / 4 h / 0 - 20 °C 5.2: 88 percent / NaOH; H2O2 / methanol; H2O / 6 h / 20 °C 6.1: DMSO; oxalyl chloride / CH2Cl2 / 1.5 h / -78 - -60 °C 6.2: Et3N / CH2Cl2 / 1 h / -60 °C 7.1: 3.27 g / acetone / 24 h / 20 °C 8.1: 96 percent / osmium tetroxide; methanesulfonamide; (DHQ)2PHAL / K2CO3; K3Fe(CN)6 / toluene; 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 9.1: Et3N; SOCl2 / CH2Cl2 / 0.5 h / 0 °C 9.2: 98 percent / RuCl3*H2O; NaIO4 / acetonitrile; CCl4; H2O / 1 h / 20 °C 10.1: NaBH4; DMAC / 0.5 h / 25 °C 10.2: 86 percent / aq. H2SO4 / 20 °C 11.1: 81 percent / H2 / Pd(OH)2/C / ethyl acetate / 10 h / 20 °C View Scheme

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potassium carbonate

potassium hydroxide

ammonia; sodium amide