1: 1.) BH3-THF, 2.) 10percent HCl / 1.) overnight, 2.) reflux, 30 min 2: 1.) sodium nitrite, acetic acid, 2.) 1 N aq. NaOH / 1.) water, RT, 10 min, 2.) methanol 3: 93 percent / pyridinium chlorochromate / CH2Cl2 / 4 h 4: 1.) NaOEt / 1.) EtOH, 5 min, 2.) RT, 90 min View Scheme

1: 1.) concd. aq. HCl, sodium nitrite, 2.) copper(I) cyanide / 1.) 5 deg C, 2.) H2O, RT, overnight 2: 1.) BH3-THF, 2.) 10percent HCl / 1.) overnight, 2.) reflux, 30 min 3: 1.) sodium nitrite, acetic acid, 2.) 1 N aq. NaOH / 1.) water, RT, 10 min, 2.) methanol 4: 93 percent / pyridinium chlorochromate / CH2Cl2 / 4 h 5: 1.) NaOEt / 1.) EtOH, 5 min, 2.) RT, 90 min View Scheme

1: 93 percent / pyridinium chlorochromate / CH2Cl2 / 4 h 2: 1.) NaOEt / 1.) EtOH, 5 min, 2.) RT, 90 min View Scheme

sodium ethanolate in ethanol Ambient temperature; Yield given. Yields of byproduct given;

sodium ethanolate 1.) EtOH, 5 min, 2.) RT, 90 min; Yield given. Multistep reaction;