1: CH2Cl2 2: H2 / Pd 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: 95 percent / tetrahydrofuran / 4 h / Heating 3: 37 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 4: 75 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 5: 96 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

in tetrahydrofuran T=0°C; Wittig reaction;