Sodium hydride → 2,3-Dimethyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridine 1-oxide

HRID 31575

Reaktionsgleichung

[CH2:1]([C:4]1([CH2:9][CH2:10][OH:11])[O:8][CH2:7][CH2:6][O:5]1)[CH2:2][CH3:3].[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N+:18]([O-:21])=[C:17]([CH3:22])[C:16]=1[CH3:23]>CS(C)=O>[CH3:22][C:17]1[C:16]([CH3:23])=[C:15]([O:11][CH2:10][CH2:9][C:4]2([CH2:1][CH2:2][CH3:3])[O:8][CH2:7][CH2:6][O:5]2)[CH:20]=[CH:19][N+:18]=1[O-:21]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a dimethylsulfoxide (22.5 ml) solution of the 2-(2-propyl-1,3-dioxolan-2-yl)ethanol (1.5 g, 9.35 mmol) obtained in the step (3b), sodium hydride, in oil (561 mg, 14 mmol as the content was regarded as 60%) and 4-chloro-2,3-dimethylpyridine1-oxide (1.33 g, 8.42 mmol) were added in a nitrogen stream and stirred at 60° C. for 2 hours. The mixture was allowed to stand at room temperature for 3 days and concentrated under reduced pressure. The residue was suspended in tetrahydrofuran. NH silica gel was added to the resultant mixture, which was then concentrated to dryness and subjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate/methanol=1/1/0→0/1/0→0/10/1) to obtain the title compound (1.53 g, yield: 58.2%) as a light brown oil.

Aufarbeitung

additionwere added in a nitrogen stream
waitto stand at room temperature for 3 days
concentrationconcentrated under reduced pressure
additionNH silica gel was added to the resultant mixture, which
concentrationwas then concentrated to dryness
washsubjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate/methanol=1/1/0→0/1/0→0/10/1)

Quellen und Nachweise

ORD-Eintrag: ord-4e1892b4d0ef48d6853a7f72d3cb1139
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07425634B2

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