Dimethyl malonate → HCID 10082482, compound

HRID 916289Notes

Reaction equation

HRID 916289 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]([O:15][CH3:16])(=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11]>CC(O)(C)C>[CH3:13][O:12][C:10]([CH:9]([C:8]([O:15][CH3:16])=[O:14])[C@@H:3]1[CH2:4][CH2:5][CH2:6][C:1](=[O:7])[CH2:2]1)=[O:11]

Participants

4

Reactant 2

HCID 7943Dimethyl malonateHCID 135942-Cyclohexen-1-one

Product 1

HCID 10082482HCID 10082482, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
30 °C

Procedure

Under an atmosphere of argon, 12.6 mg (0.02 mmol, S/C=50) of Ru[(S,S)-Tsdpen] (hexamethylbenzene), 97 μL (1.0 mmol) of 2-cyclohexenone, 114 μL (1.0 mmol) of dimethyl malonate, and 1 mL of 2-methyl-2-propanol were placed in a 20 mL Schlenk tube and stirred at 30° C. for 48 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 213 mg (93% yield) of the title compound. The optical purity was measured by HPLC (CHIRALPAK AS manufactured by Daicel Chemical Industries, Ltd., hexane: 2-propanol=85:15, flow rate 0.5 mL/min, detection at 210 nm) and it was found to be 96% ee.

Workup

  1. customThis solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2)

Sources & evidence

ORD record
ord-917bd64a9c834018a47ce94704d49c7a
Source dataset
uspto-grants-2007_09
Patent number
US07268250B2

Reaction notes

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