Oxetan-2-ylmethyl 4-methylbenzenesulfonate → 2-(Oxetan-2-ylmethyl)isoindoline-1,3-dione

HRID 424762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424762
S(O[CH2:12][CH:13]1[CH2:16][CH2:15][O:14]1)(C1C=CC(C)=CC=1)(=O)=O.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C=O)C>[C:17]1(=[O:27])[N:21]([CH2:12][CH:13]2[CH2:16][CH2:15][O:14]2)[C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12

Komponenten

4

Edukt 2

HCID 13927594Oxetan-2-ylmethyl 4-methylbenzenesulfonateHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 598409352-(Oxetan-2-ylmethyl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution of 2-(tosyloxymethyl)oxetane (27 g, 111.4 mmol) (prepared according to A. O. Fitton et al., Synthesis 1987, (12), 1140-2) and potassium phtalimide (20.64 g, 111.4 mmol) in DMF (200 ml) is stirred at a temperature of 120° C. for 18 hours, then evaporated in vacuo. The residue is taken up in ethyl acetate, the organic layer washed with water and brine, dried (Na2SO4), filtered, and evaporated to dryness. The crude solid product (19.8 g, 82%) is used in the next step without further purification.

Aufarbeitung

  1. customevaporated in vacuo
  2. washthe organic layer washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude solid product (19.8 g, 82%) is used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-c72bef309ca84da2be1ea59c7b8f74f8
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106075B2

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