Diethyl Malonate → HCID 6999756, compound

HRID 2039725Notes

Reaction equation

HRID 2039725 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 6999756HCID 6999756, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

trans-β-Nitrostyrene (34.3 mg, 0.23 mmol), diethyl malonate (0.065 mL, 0.46 mmol) and the compound (10 mol %) shown in the following Table 1 as an asymmetric catalyst were stirred in toluene (0.4 mL) at room temperature. The reaction mixture was purified by silica gel column chromatography (n-hexane/ethyl acetate=95/5→90/10→80/20) to give the title compound.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (n-hexane/ethyl acetate=95/5→90/10→80/20)

Sources & evidence

ORD record
ord-d2e41dc0b33942c8902e65e7ce3266ad
Source dataset
uspto-grants-2013_11
Patent number
US08580804B2

Reaction notes

Loading…