Isophorone → (R)-3,3,5-trimethylcyclohexanone

HRID 2253434Notes

Reaction equation

HRID 2253434 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1>CCOCC>[CH3:7][C:6]1([CH3:8])[CH2:5][C@@H:4]([CH3:10])[CH2:3][C:2](=[O:1])[CH2:9]1

Participants

3

Reactant 1

HCID 6544Isophorone

Product 1

HCID 642524(R)-3,3,5-trimethylcyclohexanoneYield 65.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared according to the general procedure from isophorone (138 mg, 1.09 mmol) in 0.2 M Et2O for 48 h at room temperature to provide the title compound as a colorless oil (100 mg, 65% yield, 97% ee) after purification by flash chromatography on silica gel (5% Et2O/pentane). The physical data were identical in all respects to those previously reported (Allinger et al. (1975), J. Org. Chem. 40:1316 (reported a rotation of +20.3° for the (S)-enantiomer that is 75% ee)). The enantiomeric ratio was determined by GLC using a Hydrodex-B-TBDAc (50 m×0.25 mm) column (110° C. isotherm, 1 mL/min.); (S) isomer tr=11.8 min. and (R) isomer tr=12.4 min. [α]D22=−18.7°(c=1.03, CHCl3).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-05e8d295024942b1b75b3d2a7d21a11f
Source dataset
uspto-grants-2008_01
Patent number
US07323604B2

Reaction notes

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