hydrogen; sodium hydride; platinum on activated charcoal 1) THF, 5 h, 59 -> 27 lb/square inch; 2) THF, reflux, 5 h; Yield given. Multistep reaction;

1: 1) H2; 2) NaH / 1) 10percent Pt-C / 1) THF, 5 h, 59 -> 27 lb/square inch; 2) THF, reflux, 5 h 2: 81 percent / KOH / ethanol / 14 h / Heating 3: 84 percent / Ac2O / 2 h / Heating 4: 90 percent / TiCl4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 1) H2; 2) NaH / 1) 10percent Pt-C / 1) THF, 5 h, 59 -> 27 lb/square inch; 2) THF, reflux, 5 h 2: 81 percent / KOH / ethanol / 14 h / Heating 3: 84 percent / Ac2O / 2 h / Heating View Scheme