Dimethyl malonate → HCID 640166, compound

HRID 916290Notes

Reaction equation

HRID 916290 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(C)=O>[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 640166HCID 640166, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
30 °C

Procedure

Under an atmosphere of argon, 24.0 mg (0.04 mmol, S/C=50) of RuH[(R,R)-Tsdpen] (1,3,5-trimethylbenzene), 194 μL (2.0 mmol) of 2-cyclohexenone, 229 μL (2.0 mmol) of dimethyl malonate, and 2 mL of acetone 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 316 mg (69% 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 73% ee.

Workup

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

Sources & evidence

ORD record
ord-6d49c74966294cd08e06f27103b3bdd2
Source dataset
uspto-grants-2007_09
Patent number
US07268250B2

Reaction notes

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