diethylamine in ethyl acetate 2 h; Heating;

formaldehyd; anhydrous diethylamine hydrochloride in water 12 h; Heating;

in tetrahydrofuran T=22°C; 1 h; Inert atmosphere;

trichlorophosphate

chloroform; tris-(2-chloro-ethyl)-amine; sulfuric acid

sulfuric acid; benzene

1: 74 percent / 4-(N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide / acetonitrile; CH2Cl2 / 1) -40 deg C, 6 h, 2) rt, 10 h 2: 1) oxalyl chloride, 2) tetrabutylammonium borohydride / 1) CH2Cl2, reflux, 2 h, 2) -78 deg C, 30 min 3: 100 percent / 4-(N,N-dimethylamino)pyridine, NEt3 / CH2Cl2; dimethylformamide / 10 h / Ambient temperature 4: DIBAL / CH2Cl2; 1,2-dimethoxy-ethane; hexane / 0.5 h / -78 °C 5: acetonitrile / 1) 10 h, rt, 2) 2 h, reflux 6: 98 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 7: 94 percent / N-bromosuccinimide / 6 h / 0 °C 8: 96 percent / AIBN, Bu3SnH / benzene / 8 h / Heating 9: LiAlH4 / diethyl ether / 1 h / 0 °C View Scheme

sulfuric acid; benzene

pyridine

1: 82 percent / dicyclohexylcarbodi-imide, 4-(N,N-dimethylamino)pyridine / acetonitrile; CH2Cl2 / -40 deg C, 6 h; room temperature, 10 h; oily substance was set aside for 5 days at room temperature 2: 1.) oxalyl chloride, 2.) tetrabutylammonium borohydride / 1.) CH2Cl2, reflux, 2 h, 2.) -78 deg C, 30 min 3: 98 percent / Ph3P, CCl4 / 15 h / Heating 4: 98 percent / tributyltin hydride, AIBN / benzene / 10 h / Heating 5: di-isobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -20 °C View Scheme