1: 63 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 2: pyridine View Scheme

1: 1) n-BuLi / 1) THF, -30 deg C, 2 h, 2) THF, -78 deg C, 2 h, then -78 dec C -> rt, 16 h 2: 97 percent / tetrahydrofuran / 4 h / Heating 3: 39 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 4: 98 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 5: 48 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

sodium hydride; dimethyl sulfoxide in tetrahydrofuran 0.5 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 40 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 2: pyridine View Scheme

sodium hydride; dimethyl sulfoxide in tetrahydrofuran 0.5 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 61 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 2: pyridine View Scheme