Ethyl cyanoacetate → HCID 278441, compound

HRID 412833Notes

Reaction equation

HRID 412833 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[CH:14]([C:12]#[N:13])[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 113722-Bromonaphthalene

Product 1

HCID 278441HCID 278441, compoundYield 917%

Reagents, catalysts & solvents 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

Method A of the above general procedure was followed using 2-bromonaphthalene (208 mg, 1.00 mmol), ethyl cyanoacetate (123 mg, 1.09 mmol), pentaphenylferrocenyl ligand (14.0 mg, 0.020 mmol) and Pd(dba)2 (6.0 mg, 0.010 mmol). The reaction mixture was purified by column chromatography on silica gel (1:3 dichloromethane/hexanes) to give the desired product (2194 mg, 91%) as a colorless oil: 1H NMR (CDCl3) δ 7.94 (s, 1H), 7.89-7.82 (m, 3H), 7.55-7.50 (m, 3H), 4.88 (s, 1H), 4.29-4.20 (m, 2H), 1.26 (t, 7.2 Hz, 3H). 13C{1H} NMR (CDCl3) δ 165.00, 133.21, 133.16, 129.35, 128.07, 127.76, 127.51, 127.21, 127.08, 126.96, 124.81, 115.75, 63.38, 43.90, 13.89.

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (1:3 dichloromethane/hexanes)

Sources & evidence

ORD record
ord-c92c0f1036364c57af69b9e33f289775
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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