Pyridine → 3-Ethyl-3-(4-iodobenzoyloxymethyl) oxetane

HRID 466512

Reaktionsgleichung

Reaktionsgleichung von HRID 466512
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([C:13]1([CH2:17][OH:18])[CH2:16][O:15][CH2:14]1)[CH3:12].N1C=CC=CC=1>CCOCC>[CH2:11]([C:13]1([CH2:17][O:18][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=2)[CH2:16][O:15][CH2:14]1)[CH3:12]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 743734-Iodobenzoyl chlorideHCID 76444Oxt-101

Produkt 1

HCID 150219453-Ethyl-3-(4-iodobenzoyloxymethyl) oxetane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 4-iodobenzoyl chloride (11.5 gms) in dry ether (50 ml) was added to a stirred solution of 3-ethyl-3-hydroxymethyloxetane (5 gms) and pyridine (3.5 mls) in ether (100 ml) at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 24 hours. After this time the mixture was washed with water and brine. The organic extracts were dried over anhydrous magnesium sulphate and then evaporated in vacuo. The residue was purified by column chromatography on silica (preeluted with 1% triethylamine in hexane) and eluted with 5% ethyl acetate in hexane. 3-Ethyl-3-(4-iodobenzoyloxymethyl) oxetane was obtained as a colourless oil (8.1 gms).

Aufarbeitung

  1. washAfter this time the mixture was washed with water and brine
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulphate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica (preeluted with 1% triethylamine in hexane)
  5. washeluted with 5% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-c0cd025686834317935ac4c1969a3a2f
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157029

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