Hydrochloric Acid → 2-Hydroxysorbinil

HRID 482695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482695
[F:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]3)[CH2:10][C:9](=[O:18])[O:8][C:5]2=[CH:6][CH:7]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>CCCCCC.O1CCCC1>[OH:18][CH:9]1[CH2:10][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[O:8]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 13644525HCID 13644525, VerbindungHCID 21225700Diisobutylaluminumhydride2×

Produkt 1

HCID 1963682-Hydroxysorbinil

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a slurry of 640 mg. (0.002 mole) of 6-fluorospiro[chroman-4,4'-imidazolidine]2,2',5'-trione in 40 ml. of toluene at -78° C. was added 852 mg. (0.006 mole) of diisobutylaluminum hydride in hexane, and the reaction mixture allowed to stir at -78° C. for 30 minutes. The reaction was allowed to warm to 0° C. and was stirred for 24 hours. The reaction was recooled to -40° C., 6 ml. of dry tetrahydrofuran was added and the reaction warmed to 0° C. Additional diisobutylaluminum hydride (1.0 ml) was added in 0.2 ml. portions. The reaction mixture was added to 10% hydrochloric acid and the mixture extracted with ethyl acetate. The combined extracts were washed dried and concentrated to dryness. The residue was chromatographed to give 67 mg. of the desired compound, m.p. 247°-251° C. (dec.).

Aufarbeitung

  1. temperatureto warm to 0° C.
  2. stirringwas stirred for 24 hours
  3. customwas recooled to -40° C.
  4. temperaturethe reaction warmed to 0° C
  5. extractionthe mixture extracted with ethyl acetate
  6. washThe combined extracts were washed
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue was chromatographed
  10. customto give 67 mg

Quellen und Nachweise

ORD-Eintrag
ord-47492f45226e4e0891b1e34bdb9d9c49
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04575507

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