Diethyl Malonate → HCID 14826591, compound

HRID 2055828Notes

Reaction equation

HRID 2055828 reaction equation
[C:1](#[N:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1(C)C=CC=CC=1>[C:1]([CH2:2][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([O:19][CH2:20][CH3:21])=[O:18])#[N:10]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 746673-Phenylprop-2-enenitrile

Product 1

HCID 14826591HCID 14826591, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

[(S,S)-N-methanesulfonyl-1,2-diphenylethylenediamine]-(hexamethylbenzene)ruthenium (5.5 mg, 0.01 mmol, S/C=50), cinnamonitrile (65 μl, 0.5 mmol), diethyl malonate (76 μl, 0.5 mmol) and toluene (0.5 ml) were added into Schlenk (20 ml) under an argon atmosphere, and stirred at 30° C. for 48 hours. 1HNMR determination of the solution showed that the yield of the product was 46%. The reaction solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2), and the optical purity was measured by HPLC (CHIRALPACK AS manufactured by Daicel Co., Ltd., hexane:2-propanol=90:10, flow rate 0.5 ml/min, detection by 210 nm), resulting to 56% ee.

Workup

  1. customThe reaction solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2)
  2. customresulting to 56% ee

Sources & evidence

ORD record
ord-a2a175710ae24cb69325d681b4f5f3bd
Source dataset
uspto-grants-2008_02
Patent number
US07332622B2

Reaction notes

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