Water → 5-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-5-phenylvaleronitrile

HRID 1464525

Reaktionsgleichung

I[CH2:2][CH2:3][CH2:4][CH:5]([C:12]1[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[C:15]([CH3:21])=[C:14]([CH3:22])[C:13]=1[O:23][CH3:24])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C-:25]#[N:26].[Na+].C(OC(C)C)(C)C.O>CS(C)=O>[CH3:24][O:23][C:13]1[C:14]([CH3:22])=[C:15]([CH3:21])[C:16]([O:19][CH3:20])=[C:17]([CH3:18])[C:12]=1[CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][CH2:3][CH2:2][C:25]#[N:26]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 4.19 g (5.0 mmole) of 1-iodo-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-4-phenylbutane in dimethylsulfoxide (30 ml) was added 0.74 g (5×3 mmole) of sodium cyanide, and the mixture was stirred at 50° C. for 2 hours. The reaction solution was cooled with ice, and isopropyl ether and water were added to it, followed by stirring. The isopropyl ether layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residual solution was chromatographed on a silica gel column to perform purification (elution with isopropyl ether/hexane) to thereby give 1.65 g (98%) of 5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-phenylvaleronitrile. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 14.

Aufarbeitung

additionwere added to it
stirringby stirring
customThe isopropyl ether layer was separated out
washwashed with aqueous sodium chloride solution
dry with materialdried (magnesium sulfate)
customevaporated
customThe residual solution was chromatographed on a silica gel column
custompurification (elution with isopropyl ether/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-316c513b3521443883167070cb77e4ff
Quelldatensatz: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05304658

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