Diethyl Malonate → HCID 10377694, compound

HRID 916291Notes

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(C)=O>[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 RuH[(R,R)-Tsdpen] (1,3,5-trimethylbenzene), 194 μL (2.0 mmol) of 2-cyclohexenone, 304 μL (2.0 mmol) of diethyl 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 330 mg (64% yield) of the title compound. After this was converted into an ethylene ketal derivative as shown below, 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 77% ee.

Workup

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

Sources & evidence

ORD record: ord-3b384cd47bee4702904a1ed0289bb089
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268250B2

Reaction notes

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