hydrogen; platinum(IV) oxide in methanol P=5171.48 Torr;

1.1: MeLi / tetrahydrofuran; diethyl ether / 2 h / -50 °C 1.2: tetrahydrofuran; diethyl ether / -50 - 20 °C 2.1: hydrogen / PtO2 / methanol / 5171.48 Torr View Scheme

1: 72 percent / LDA / hexane; tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to r.t., 1 h 2: 1.) SnCl4, 2.) H2O / 1.) CH2Cl2, -78 deg C, 20 min; -78 to 10 deg C, 3 h, 2.) CH2Cl2, reflux, 2 h 3: NaBH4 View Scheme

sodium tetrahydroborate

1: 1.) SnCl4, 2.) H2O / 1.) CH2Cl2, -78 deg C, 20 min; -78 to 10 deg C, 3 h, 2.) CH2Cl2, reflux, 2 h 2: NaBH4 View Scheme