HCID 12093580, compound → HCID 22935669, compound

HRID 853740Notes

Reaction equation

HRID 853740 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

4

Reactant 2

HCID 12093580HCID 12093580, compoundHCID 16684438Red-Al

Product 1

HCID 22935669HCID 22935669, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

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.

Workup

  1. customat 60-70° C

Sources & evidence

ORD record
ord-415b60cac4b243038b67879252678d6e
Source dataset
uspto-grants-2007_08
Patent number
US07256170B2

Reaction notes

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