Dimethyl malonate → HCID 10398317, compound

HRID 916301Notes

Reaction equation

HRID 916301 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[C:7]([O:14][CH3:15])(=[O:13])[CH2:8][C:9]([O:11][CH3:12])=[O:10]>CC(O)(C)C>[CH3:12][O:11][C:9]([CH:8]([C:7]([O:14][CH3:15])=[O:13])[C@@H:3]1[CH2:4][CH2:5][C:1](=[O:6])[CH2:2]1)=[O:10]

Participants

4

Reactant 2

HCID 7943Dimethyl malonateHCID 135882-Cyclopenten-1-one

Product 1

HCID 10398317HCID 10398317, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
30 °C

Procedure

Under an atmosphere of argon, 11.0 mg (0.02 mmol, S/C=100) of Ru[(S,S)-Msdpen] (hexamethylbenzene), 168 μL (2.0 mmol) of 2-cyclopentenone, 228 μl (2.0 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 72 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 425 mg (99% yield) of the title compound. The optical rotation [α]D21 was +96.3 (c 0.54, CHCl3). The optical purity was measured by HPLC (CHIRALPAK AS manufactured by Daicel Chemical Industries, Ltd., hexane:2-propanol=80:20, flow rate 1.0 mL/min, detection at 210 nm) and it was found to be 98% ee.

Workup

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

Sources & evidence

ORD record
ord-fbc8d58e81554b3e96efba517b6453d7
Source dataset
uspto-grants-2007_09
Patent number
US07268250B2

Reaction notes

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