Triethylene Glycol → 2-(3-Pyridylmethyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

HRID 35193

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19]4([CH3:24])[O:23][CH2:22][CH2:21][O:20]4)[CH:15]=3)[CH:10]=2)=O)[CH:2]=1.C(O)COCCOCCO.NN.[OH-].[K+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19]4([CH3:24])[O:20][CH2:21][CH2:22][O:23]4)[CH:15]=3)[CH:10]=2)[CH:2]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 270 mg of 2-(3-pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene, 7 ml of triethylene glycol, 1 ml of anhydrous hydrazine and 500 mg of potassium hydroxide were heated at 160° C. for 30 minutes. The temperature was then raised to 210° C. for 1 hour. The mixture was cooled, poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, the solvent removed under reduced pressure and the residue chromatographed on silica gel to give 160 mg of 2-(3-pyridylmethyl)-6-(2-methyl-1,3dioxolan-2-yl)naphthalene as an oil.

Workup

temperatureThe temperature was then raised to 210° C. for 1 hour
temperatureThe mixture was cooled
extractionextracted with methylene chloride
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent removed under reduced pressure
customthe residue chromatographed on silica gel

Sources & evidence

ORD record: ord-9b438c38abb14a318e2a01f24f8f5b42
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04766127

Linked notes

Loading…