Dimethyl malonate → HCID 10399470, compound

HRID 916305Notes

Reaction equation

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

Participants

Conditions

Temperature: 30 °C

Procedure

Under an atmosphere of argon, 11.0 mg (0.02 mmol, S/C=50) of Ru[(S,S)-Msdpen] (hexamethylbenzene), 122 μL (1.0 mmol) of 4,4-dimethyl-2-cyclopentenone, 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 72 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 202 mg (83% yield) of the title compound. The optical rotation [α]D25 was +101.6 (c 1.04, CHCl3). 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 99% ee.

Workup

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

Sources & evidence

ORD record: ord-e2ee34fe774c436db6a91535df05fe38
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268250B2

Reaction notes

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