Hydrochloric Acid → 2-(4-Ethoxyphenyl)propanenitrile

HRID 622745Notes

Reaction equation

[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1)[CH3:14].CI.Cl>O1CCCC1>[CH2:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:1])[C:23]#[N:24])=[CH:18][CH:17]=1)[CH3:14]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 8.8 g of diisopropylamine in 150 ml of dry tetrahydrofuran were added 50 ml (1.5 mmole/ml) of n-butyl lithium at -50° C. After stirring at -20° C. for 30 minutes, 10.0 g of 4-ethoxyphenylacetonitrile was added thereto at -50° C. After stirring at the same temperature for 1 hour, 10.1 g of methyl iodide was added dropwise at -50° C. After stirring at the same temperature for 3 hours and then at 20° C. for 10 hours, the reaction solution was poured into 10% aqueous hydrochloric acid and extracted with ethyl acetate. After concentrating the ethyl acetate layer, the residual oil was column-chromatographed on silica gel (developing solvent, n-hexane: ethyl acetate=20:1) to obtain 9.50 g of the desired 2-(4-ethoxyphenyl) propionitrile [corresponding to the compound represented by the foregoing formula (II) wherein R1 is an ethoxy group, R2 is a hydrogen atom and R4 is a methyl group] as a pale yellow oil.

Workup

customat -50° C
stirringAfter stirring at the same temperature for 1 hour
stirringAfter stirring at the same temperature for 3 hours
waitat 20° C. for 10 hours
extractionextracted with ethyl acetate
concentrationAfter concentrating the ethyl acetate layer
customthe residual oil was column-chromatographed on silica gel (developing solvent, n-hexane: ethyl acetate=20:1)

Sources & evidence

ORD record: ord-3f8ebeb7827b431396519def9b31ecc1
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04772633

Reaction notes

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