1: With sodium hydroxide; water in tetrahydrofuran; methanol T=20°C; 15 h; 2: With hydrogenchloride in tetrahydrofuran; methanol; water pH=3;

1: 93 percent / LiBH4 / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) reflux, 4 h 2: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 45 min, -78 deg C to room temperature, 10 min View Scheme

lithium borohydride in tetrahydrofuran 1.) 0 deg C, 2 h, 2.) reflux, 4 h;