cyclohexanone; acetic acid in diethyl ether

1: 64 percent / tetrahydrofuran / 2 h / Ambient temperature 2: piperidine acetate / xylene / 4 h / Heating 3: TsOH / 24 h / Ambient temperature 4: 93 percent / DIBAH / diethyl ether; toluene / 1.5 h / -20 °C 5: 97 percent / pyridine / 18 h / -5 - 0 °C 6: 82 percent / LiAlH4 / diethyl ether / 1.5 h 7: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h 8: 92 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 64 percent / tetrahydrofuran / 2 h / Ambient temperature 2: piperidine acetate / xylene / 4 h / Heating 3: TsOH / 24 h / Ambient temperature 4: 93 percent / DIBAH / diethyl ether; toluene / 1.5 h / -20 °C 5: 97 percent / pyridine / 18 h / -5 - 0 °C 6: 82 percent / LiAlH4 / diethyl ether / 1.5 h 7: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h 8: 76 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme

1: 64 percent / tetrahydrofuran / 2 h / Ambient temperature 2: piperidine acetate / xylene / 4 h / Heating 3: TsOH / 24 h / Ambient temperature 4: 93 percent / DIBAH / diethyl ether; toluene / 1.5 h / -20 °C 5: 97 percent / pyridine / 18 h / -5 - 0 °C 6: 82 percent / LiAlH4 / diethyl ether / 1.5 h 7: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h View Scheme

magnesium; ethylene dibromide in tetrahydrofuran T=30 - 40°C; 4 h; Inert atmosphere;

1: phosphorus tribromide / toluene / 1 h / -10 °C / |Inert atmosphere 2: magnesium; ethylene dibromide / tetrahydrofuran / 4 h / 30 - 40 °C / |Inert atmosphere View Scheme

1: 64 percent / tetrahydrofuran / 2 h / Ambient temperature 2: piperidine acetate / xylene / 4 h / Heating 3: TsOH / 24 h / Ambient temperature 4: 93 percent / DIBAH / diethyl ether; toluene / 1.5 h / -20 °C 5: 97 percent / pyridine / 18 h / -5 - 0 °C 6: 82 percent / LiAlH4 / diethyl ether / 1.5 h View Scheme

(i), (ii) (esterification); Multistep reaction;

Yield given. Multistep reaction;

cyclohexanone; acetic acid in diethyl ether