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

HRID 1645514Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 60 °C

Procedure

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-dimethylpyridine 1-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.

Workup

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)

Sources & evidence

ORD record: ord-8cf0166e98bd4c1792ed4cbb94295e25
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124780B2

Reaction notes

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