Diethyl Malonate → Diethyl [(4-cyanophenyl)methyl]propanedioate

HRID 1256880Notes

Reaction equation

HRID 1256880 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1)#[N:13]>>[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:16][CH:15]=1)#[N:13]

Participants

3

Reactant 2

HCID 7761Diethyl MalonateHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 14370114Diethyl [(4-cyanophenyl)methyl]propanedioateYield 66.3%

Procedure

In the same manner as in Example 6 (1), a crude product was obtained using diethyl malonate (13.6 g) and 4-cyanobenzyl bromide (16.7 g). This was purified by silica gel column chromatography to give the title compound (15.5 g) as an oil.

Workup

  1. customThis was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-17856c63e9f7444084c4e1997d7152dc
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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