HCID 86731814, compound → HCID 86731813, compound

HRID 1527825Notes

Reaction equation

HRID 1527825 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][C:6]([C:8](=[O:15])[CH2:9][CH2:10][CH:11]([CH3:14])[CH:12]=[O:13])=[CH:5][CH2:4][CH2:3]1>C1(C)C=CC=CC=1>[CH3:16][C:2]1([CH3:1])[CH2:7][C:6]([C:8](=[O:15])[CH2:9][CH2:10][CH:11]([CH3:14])[CH2:12][OH:13])=[CH:5][CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 86731814HCID 86731814, compound

Product 1

HCID 86731813HCID 86731813, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

5-(5,5-dimethylcyclohex-1-en-1-yl)-2-methyl-5-oxopentanal (6.67 g, 0.03 mol.), toluene (20 g, 300 wt. %) and (ethylenediamine)[1,2-bis(diphenylphosphino)ethane]ruthenium (bispivalate) (2.3 mg, 0.003 mmol, 0.01 mol.%) were loaded altogether in a 125 ml autoclave equipped with a mechanical stirring device. Sealed autoclave was then purged to under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to 50 bars hydrogen. It was then heated to 100° C. and hydrogen pressure was maintained to 50 bars during all the reaction to afford desired product with 90.0% selectivity. Upon reaction completion (checked by both hydrogen consumption and GC), autoclave was then cooled down to 25° C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and solvent was removed under vacuum. After flash chromatography, 1-(5,5-dimethylcyclohex-1-en-1-yl)-5-hydroxy-4-methylpentan-1-one was obtained in 85% yield.

Workup

  1. customequipped with a mechanical stirring device
  2. customSealed autoclave
  3. customwas then purged
  4. temperaturehydrogen pressure was maintained to 50 bars during all
  5. customthe reaction

Sources & evidence

ORD record
ord-5208788f2d104ac18b60e34e1a2c49bd
Source dataset
uspto-grants-2015_07
Patent number
US09090534B2

Reaction notes

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