1: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 2: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 3: 82 percent / diethyl ether / 0.25 h / 0 °C 4: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 5: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 6: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 7: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 8: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 9: 95 percent / aq. sodium hydroxide / 0.08 h View Scheme

sodium acetate; 5-(2-hydroxyethyl)-4-methyl-3-(phenylmethyl)thiazolium chloride in ethanol 1.5 h; Heating;

1: trimethylsilyl cyanide; phenylacetaldehyde With triethylamine in dichloromethane T=0°C; 2 h; 2: chloro(phenylmethyl)-magnesium in diethyl ether 2 h; Heating;

sodium; 4,4'-di-tert-butylbiphenyl in tetrahydrofuran 12 h; Ambient temperatureIrradiationultrasonic irradiation;

chloro-trimethyl-silane

in tetrahydrofuran 3 h; Heating;

in tetrahydrofuran PhCH2Br was added dropwise to a THF soln. of Ni-complex at -78°C under Ar, mixt. was warmed slowly and allowed to react for 5 h; mixt. was poured onto solid iodine, stirred for 15 min, washed with aq. NaHSO3, aq. layers were washed with ether, ether ext. was combined with THF soln. and dried over K2CO3; BuC(O)CH2Ph was tentatively identified by GC-MS;

N,N,N',N',N'',N''-hexamethylphosphoric triamide in diethyl ether

diethyl ether anschliessend Behandeln mit wss.HCl unter Kuehlung;

hydrogenchloride 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight; Yield given. Multistep reaction;