Diethyl Malonate → HCID 10377693, compound

HRID 916292Notes

Reaction equation

[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]>CC(O)(C)C>[CH2:17]([O:16][C:8]([CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C@@H:3]1[CH2:4][CH2:5][CH2:6][C:1](=[O:7])[CH2:2]1)=[O:15])[CH3:18]

Participants

Conditions

Temperature: 30 °C

Procedure

Under an atmosphere of argon, 24.0 mg (0.04 mmol, S/C=50) of Ru[(S,S)-Tsdpen](p-cymene), 194 μL (2.0 mmol) of 2-cyclohexenone, 304 μL (2.0 mmol) of diethyl malonate, and 2 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 409 mg (80% yield) of the title compound. After this was converted into an ethylene ketal derivative as shown 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 61% ee.

Workup

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

Sources & evidence

ORD record: ord-ee9a2bbe2bf84c60b5fcde9f2480a99c
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268250B2

Reaction notes

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