Dimethyl malonate → Propanedioic acid, [1-(4-methylphenyl)-2-nitroethyl]-, dimethyl ester

HRID 2055829Notes

Reaction equation

HRID 2055829 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:13]([O:20][CH3:21])(=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C1(C)C=CC=CC=1>[CH3:18][O:17][C:15]([CH:14]([CH:6]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:12][CH:11]=1)[CH2:7][N+:8]([O-:10])=[O:9])[C:13]([O:20][CH3:21])=[O:19])=[O:16]

Participants

4

Reactant 2

HCID 7943Dimethyl malonateHCID 2867351-Methyl-4-(2-nitroethenyl)benzene

Product 1

HCID 3304889Propanedioic acid, [1-(4-methylphenyl)-2-nitroethyl]-, dimethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

[(S,S)-N-(pentamethylbenzenesulfonyl)-1,2-diphenyl-ethylenediamine](hexamethylbenzene)ruthenium (13.7 mg, 0.02 mmol, S/C=50), 4-methyl-β-nitrostyrene (1.0 mmol), dimethyl malonate (114 μl, 1.0 mmol) and toluene (1 ml) were added into Schlenk (20 ml) under an argon atmosphere, and stirred at −20° C. for 48 hours. The reaction solution was purified by flash column chromatography (hexane/acetone=80/20, SiO2), showing that the isolation yield of the product was 71%. The optical purity was measured by HPLC (CHIRALPACK AD manufactured by Daicel Co., Ltd., hexane:2-propanol=90:10, flow rate 0.5 ml/min, detection by 210 nm), resulting to 92% ee.

Workup

  1. customThe reaction solution was purified by flash column chromatography (hexane/acetone=80/20, SiO2)
  2. customresulting to 92% ee

Sources & evidence

ORD record
ord-eaf3f65dedb74d3ba7300bf71b37dcc6
Source dataset
uspto-grants-2008_02
Patent number
US07332622B2

Reaction notes

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