HCID 12093580, compound → 10-Ethyl-8-methyl-spiro[4.5]dec-7-en-1-ol

Reaction equation

[CH2:1]([CH:3]1[C:8]2([C:12](=[O:13])[CH2:11][CH2:10][CH2:9]2)[CH2:7][CH:6]=[C:5]([CH3:14])[CH2:4]1)[CH3:2].COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([CH:3]1[C:8]2([CH:12]([OH:13])[CH2:11][CH2:10][CH2:9]2)[CH2:7][CH:6]=[C:5]([CH3:14])[CH2:4]1)[CH3:2]

Participants

Procedure

10-Ethyl-8-methyl-spiro[4.5]dec-7-en-1-one (14 g; 0.073 mol) was dissolved in toluene (60 ml) and reduced using Vitride® in toluene; 40 ml) at 60-70° C. A partial conversion was observed: 22.1% ketones and 67.5% alcohols. Usual work-up (see above), followed by column chromatography on SiO2 (solvent: hexane/MTBE: 9/1) afforded 95.6% pure desired product, as a mixture of isomers.