Phosphoric Acid → 6-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1781411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1781411
[C-]#N.[Na+].Br[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10](=[O:15])[CH2:9][CH2:8]2.OP(O)(O)=O.BrC1CCC2C(=CC=CC=2)C1=O.[C:33](C1CCC2C(=CC=CC=2)C1=O)#[N:34]>C1(C)C=CC=CC=1.O.CC#N>[C:33]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10](=[O:15])[CH2:9][CH2:8]2)#[N:34]

Komponenten

9

Edukt 5

HCID 1004Phosphoric AcidHCID 8929Sodium CyanideHCID 1011201(2H)-Naphthalenone, 2-bromo-3,4-dihydro-HCID 27335536-Bromo-2-tetraloneHCID 122310271-Oxo-1,2,3,4-tetrahydro-naphthalene-2-carbonitrile

Produkt 1

HCID 162445046-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A flame dried 1 liter round bottom flask with argon inlet, digital thermometer, and magnetic stir bar, was charged with a 68% NaCN/alumina mixture (21.22 g, 433 mmol)(NaCN and alumina were ground together in a morter and pestle according to the procedure of Dalton et al. J. Org. Chem., 44, (24) 4443(1979)), and tetrakis(triphenylphospine) palladium(0) (10.0 g, 8.65 mmol). The flask was purged three times via vacuum with argon and a solution of 6-bromo-2-tetralone (19.46 g, 86.5 mmol) in degassed toluene (400 mL) was added. The mixture was heated to 80° C. and stirred for 64 hrs at that temperature. Analysis by HPLC indicated 89% conversion (HPLC conditions, column: Waters C18 Bondapak, eluent: 80:20 (0.1% H3PO4 in H2O: CH3CN), flow: 2 mL/min, wavelength: 220 nm, Rt: bromotetralone=9.65 min, cyanotetralone=3.46 min). The reaction was cooled and the mixture filtered through silfca gel (elution with 60% ethyl acetate in hexane.) Concentration of the appropriate fractions gave 9.4 g (68%) of 6-cyano-2-tetralone (98.7% by HPLC).

Aufarbeitung

  1. customA flame dried 1 liter round bottom flask with argon inlet
  2. customThe flask was purged three times via vacuum with argon
  3. temperatureThe reaction was cooled
  4. filtrationthe mixture filtered through silfca gel (elution with 60% ethyl acetate in hexane.) Concentration of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-71eeed9b844b4aeeb9efd514647a519b
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05633247

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