Pyridine → (3-Ethyloxetan-3-yl)methyl 3-pyridinecarboxylate

HRID 345288

Reaktionsgleichung

Reaktionsgleichung von HRID 345288
Cl.[CH2:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH2:10]([C:12]1([CH2:16][OH:17])[CH2:15][O:14][CH2:13]1)[CH3:11].N1C=CC=CC=1.C(=O)([O-])[O-:25].[Na+].[Na+]>ClCCl>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([O:17][CH2:16][C:12]2([CH2:10][CH3:11])[CH2:15][O:14][CH2:13]2)=[O:25])[CH:4]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 76444Oxt-101

Produkt 1

HCID 19992002(3-Ethyloxetan-3-yl)methyl 3-pyridinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Nicotinyl chloride hydrochloride (8.9 gm.) was added to a stirred solution of 3-ethyl-3-hydroxymethyloxetane (5.8 gm.) and dry pyridine (20 ml.) in dry dichloromethane (150 ml.) at 0°. The mixture was stirred at room temperature for 4 days and poured into aqueous sodium carbonate solution. The aqueous mixture was extracted with dichloromethane. The extracts were washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. The residue was purified by chromatography on silica eluting with 5% triethylamine in dichloromethane. (3-Ethyloxetan-3-yl)methyl 3-pyridinecarboxylate was obtained as a pale yellow oil (7.0 gm.).

Aufarbeitung

  1. extractionThe aqueous mixture was extracted with dichloromethane
  2. washThe extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by chromatography on silica eluting with 5% triethylamine in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e348c7bc47ba44ad998de5232bb87078
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05057504

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