hydrogen; palladium 10 on activated carbon in ethanol T=20°C;

1: 95 percent / DIBAL-H / diethyl ether; hexane / 1 h / 0 °C 2: 94 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 3: 99 percent / toluene / Heating 4: DIBAL-H / diethyl ether; hexane / 1 h / 0 °C 5: 9.9 g / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 6: 92 percent / toluene / Heating 7: 97 percent / DIBAL-H / diethyl ether; hexane / 1 h / 20 °C View Scheme

1: 95 percent / DIBAL-H / diethyl ether; hexane / 1 h / 0 °C 2: 94 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 3: 99 percent / toluene / Heating 4: DIBAL-H / diethyl ether; hexane / 1 h / 0 °C 5: 9.9 g / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 6: 92 percent / toluene / Heating 7: 97 percent / DIBAL-H / diethyl ether; hexane / 1 h / 20 °C 8: 57 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C View Scheme

1: 95 percent / DIBAL-H / diethyl ether; hexane / 1 h / 0 °C 2: 94 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C View Scheme

1: 95 percent / DIBAL-H / diethyl ether; hexane / 1 h / 0 °C 2: 94 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 3: 99 percent / toluene / Heating 4: DIBAL-H / diethyl ether; hexane / 1 h / 0 °C 5: 9.9 g / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C View Scheme

1: 95 percent / DIBAL-H / diethyl ether; hexane / 1 h / 0 °C 2: 94 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 3: 99 percent / toluene / Heating 4: DIBAL-H / diethyl ether; hexane / 1 h / 0 °C View Scheme