1: tBuOCl / methanol 2: Na2CO3 / xylene / Heating 3: LiAlH4 / diethyl ether 4: MnO2 / petroleum ether View Scheme

1: methyllithium With thien-2-yl(cyano)copper lithium in tetrahydrofuran; diethyl ether T=-78°C; 0.166667 h; 2: ethyl 6-oxocyclohex-1-ene-1-carboxylate in tetrahydrofuran; diethyl ether T=-78 - 20°C; 1.08333 h; 3: With ammonia; water; ammonium chloride in tetrahydrofuran; diethyl ether

1: 1) O3, 2) (CH3)2S / 1) CH2Cl2, - 78 deg C, 2) -78 deg C to RT, 3 h 2: 15.1 g / benzene / 12 h / Heating 3: 1) anhydr. CuCl / 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C View Scheme

1: 15.1 g / benzene / 12 h / Heating 2: 1) anhydr. CuCl / 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C View Scheme

copper(l) chloride 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C; Yield given. Multistep reaction;

1: tBuOCl / methanol 2: Na2CO3 / xylene / Heating 3: LiAlH4 / diethyl ether View Scheme