HCID 11120848, compound → HCID 14758908, compound

Participants

Reaction Steps

Catalytic Transfer Hydrogenolysis Protocol: 48.5 mg of Pd(OH)2 on activated charcoal (20%) (Pearlman's catalyst) is added to a solution of (S)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-4-methyl-pentane 5 (485 mg, 1.5 mmol) in 12.0 ml of absolute ethanol and 6.0 ml of cyclohexene. The mixture is heated under ref lux until the reaction is completed (tic monitoring). If starting material can still be detected after 8 h, some catalyst is added and refluxing is continued until the reaction is completed. After cooling to room temperature the catalyst is filtered off. The filtrate is concentrated in vacuo. Purification of the residue by flash column chromatography (pentane/diethyl ether 5:1) affords (S)-5-(tert-butyldimethylsilyloxy)4-methyl-pentan-1-ol 6 (565 mg, 97%) as a colourless oil.

Provenance & Evidence