Potassium Hydroxide → HCID 11536549, compound

HRID 646184Notes

Reaction equation

HRID 646184 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[CH2:11]([O:13][CH2:14][N:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O)[CH3:12].C1OCCOCCOCCOCCOCCOC1.[OH-].[K+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:20]/[C:16]2[N:15]([CH2:14][O:13][CH2:11][CH3:12])[CH:19]=[CH:18][CH:17]=2)/[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 2415824-Chlorobenzyl cyanideHCID 64983039HCID 64983039, compound

Product 1

HCID 11536549HCID 11536549, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chlorophenylacetonitrile (500 mg, 3.30 mmol), 1-ethoxymethyl-1H-pyrrole-2-carbaldehyde (520 mg, 3.39 mmol, 1.03 equiv.), and 18-crown-6 ether as a phase transfer catalyst (87 mg, 0.33 mmol) in toluene (30 ml) was added potassium hydroxide (185 mg, 3.30 mmol) and the mixture was heated to 80° C. for 3 h, then stirred at room temperature overnight. The solution was filtered through a small plug of silica and concentrated to afford an oil (705 mg). This is Compound 7 in Table 8.

Workup

  1. filtrationThe solution was filtered through a small plug of silica
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a8c43e4f364e4ae095cfe9da5a4abae8
Source dataset
uspto-grants-2010_04
Patent number
US07705038B2

Reaction notes

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