1: With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran; cyclohexane T=-78 - -72°C; 3 h; 2: With B(OMe)3 in tetrahydrofuran; cyclohexanone T=-78 - 0°C; 3: With dihydrogen peroxide; acetic acid in tetrahydrofuran; cyclohexane; water T=20°C;

N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran; cyclohexane -78 deg C to room temp., then overnight;

1: 86 percent / Amberlyst-15 / benzene / 12 h / Heating 2: 1.) NaH, 2.) DMAP / 1.) THF, 0 deg C, 2.) THF, 0 deg C to room temp., 20 h 3: 70 percent / K2CO3, CuO / dimethylformamide / 1.5 h / Heating 4: 58 percent / TMEDA, sec-BuLi / tetrahydrofuran; cyclohexane / -78 deg C to room temp., then overnight View Scheme

1: 70 percent / K2CO3, CuO / dimethylformamide / 1.5 h / Heating 2: 58 percent / TMEDA, sec-BuLi / tetrahydrofuran; cyclohexane / -78 deg C to room temp., then overnight View Scheme

1: 1.) NaH, 2.) DMAP / 1.) THF, 0 deg C, 2.) THF, 0 deg C to room temp., 20 h 2: 70 percent / K2CO3, CuO / dimethylformamide / 1.5 h / Heating 3: 58 percent / TMEDA, sec-BuLi / tetrahydrofuran; cyclohexane / -78 deg C to room temp., then overnight View Scheme

1: 1.) NaH, 2.) DMAP / 1.) THF, 0 deg C, 2.) THF, 0 deg C to room temp., 20 h 2: 70 percent / K2CO3, CuO / dimethylformamide / 1.5 h / Heating 3: 58 percent / TMEDA, sec-BuLi / tetrahydrofuran; cyclohexane / -78 deg C to room temp., then overnight View Scheme

1: SOCl2 / CHCl3 2: diethyl ether View Scheme

1: diethyl ether View Scheme

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