Water → Methyl 3-(p-Cyanophenyl)-2-(p-cyanobenzoyl)propionate

HRID 569499Notes

Reaction equation

HRID 569499 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:16]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)#[N:17].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[C:16]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][CH:9]([C:7](=[O:8])[C:6]2[CH:14]=[CH:15][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[C:10]([O:12][CH3:13])=[O:11])=[CH:20][CH:19]=1)#[N:17]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 2757970Methyl 3-(4-cyanophenyl)-3-oxopropanoate

Product 1

HCID 13533626Methyl 3-(p-Cyanophenyl)-2-(p-cyanobenzoyl)propionate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl p-cyanobenzoylacetate 17.77 g, 0.087 mole) and p-cyanobenzyl bromide (17.16 g, 0.087 mole) were combined in 525 ml DMF under N2 . K2CO3 (12.1 g, 0.087 mole) was added, the slurry stirred 1.5 hours and finally poured into a mixture of 2.5 liters H2O and 0.5 liter ethyl acetate. The organic layer was separated, washed with fresh H2O and then brine, stripped to dryness, and the residue slurried in ether to yield title product: 14.83 g (53.6%); m.p. 154°-157°; tlc (4:1 toluene:ethyl acetate) Rf 0.44.

Workup

  1. customThe organic layer was separated
  2. washwashed with fresh H2O

Sources & evidence

ORD record
ord-11c5b9a18a334f219dcaa219adea7d7c
Source dataset
uspto-grants-1988_03
Patent number
US04732907

Reaction notes

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