Dimethylhydantoin → 3-Allyl-5,5-dimethylhydantoin

HRID 1597411

Reaktionsgleichung

Reaktionsgleichung von HRID 1597411
[CH2:1](O)[CH2:2][CH:3]=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:25][C:26]1([CH3:33])[NH:30][C:29](=[O:31])[NH:28][C:27]1=[O:32].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH2:3]([N:28]1[C:27](=[O:32])[C:26]([CH3:33])([CH3:25])[NH:30][C:29]1=[O:31])[CH:2]=[CH2:1]

Komponenten

7

Edukt 4

HCID 6491DimethylhydantoinHCID 11776TriphenylphosphineHCID 693893-Buten-1-olHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 5976963-Allyl-5,5-dimethylhydantoinAusbeute 106,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-buten-1-ol (1 g, 13.9 mmol), triphenylphosphine (4.73 g, 18 mmol) and 5,5-dimethylhydantoin (2.1 g, 16.7 mmol) in THF (50 mL) was treated dropwise with diethylazodicarboxylate (3.13 g, 18.0 mmol), stirred at ambient temperature for 1 hour, treated with water and partitioned between ethyl acetate and brine. The organic layer was dried (Na2SO4), filtered, and concentrated to provide crude product which was purified on silica gel with 50% ethyl acetate/hexanes to provide 2.5 g (100%) of the title compound.

Aufarbeitung

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide crude product which
  6. customwas purified on silica gel with 50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-16810d9117894fc99bebd0a360c69f20
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294573B1

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