Diethyl Malonate → HCID 6995515, compound

HRID 2055826Notes

Reaction equation

HRID 2055826 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[C:12]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:12]([CH:13]([C@H:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][N+:1]([O-:3])=[O:2])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 5284459beta-nitrostyrene, (E)-

Product 1

HCID 6995515HCID 6995515, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

[(S,S)-N-(pentamethylbenzenesulfonyl)-1,2-diphenylethylenediamine](hexamethylbenzene)ruthenium (13.7 mg, 0.02 mmol, S/C=50), trans-β-nitrostyrene (149 mg, 1.0 mmol), diethyl malonate (152 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 yield of the product was 89%. The optical purity was measured by HPLC (CHIRALPACK AD manufactured by Daicel Co., Ltd., hexane:2-propanol=95:5, flow rate 0.5 ml/min, detection by 210 nm), resulting to 93% ee.

Workup

  1. customThe reaction solution was purified by flash column chromatography (hexane/acetone=80/20, SiO2)
  2. customresulting to 93% ee

Sources & evidence

ORD record
ord-9bfc1dc1a29e4d7db2c9a86077c84ebf
Source dataset
uspto-grants-2008_02
Patent number
US07332622B2

Reaction notes

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