Diethyl Malonate → HCID 11776499, compound

HRID 916297Notes

Reaction equation

HRID 916297 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[C:7]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>CC(C)=O>[CH2:16]([O:15][C:7]([CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@H:3]1[CH2:4][CH2:5][C:1](=[O:6])[CH2:2]1)=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 135882-Cyclopenten-1-one

Product 1

HCID 11776499HCID 11776499, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °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), 168 μL (2.0 mmol) of 2-cyclopentenone, 304 μL (2.0 mmol) of diethyl malonate, and 2 mL of acetone were placed in a 20 mL Schlenk tube and stirred at 40° C. for 24 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 462 mg (95% yield) of the title compound. After this was converted into an ethylene ketal derivative by the same procedure as in Example 3, the optical purity was measured by HPLC (CHIRALCEL OD manufactured by Daicel Chemical Industries, Ltd., hexane:2-propanol=97: 3, flow rate 0.5 mL/min, detection at 210 nm) and it was found to be 91% ee.

Workup

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

Sources & evidence

ORD record
ord-bab12a9fa40440b498955919e43eb2d3
Source dataset
uspto-grants-2007_09
Patent number
US07268250B2

Reaction notes

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