Dimethylformamide → N,N-Dimethyl-2-[2-(2-naphthyl)ethenyloxy]ethanamine

HRID 368913

Reaktionsgleichung

Reaktionsgleichung von HRID 368913
O([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)S(C(F)(F)F)(=O)=O.[CH3:19][N:20]([CH3:26])[CH2:21][CH2:22][O:23][CH:24]=[CH2:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>CCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][N:20]([CH3:26])[CH2:21][CH2:22][O:23][CH:24]=[CH:25][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 19240Dimethylaminoethyl vinyl etherHCID 45463412-Naphthyl Trifluoromethanesulfonate

Produkt 1

HCID 54382846N,N-Dimethyl-2-[2-(2-naphthyl)ethenyloxy]ethanamineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8003PentaneLösungsmittel

Versuchsvorschrift

Table 1, Entry 7. In the reaction tube were mixed 2-naphthyl triflate (0.276 g, 1.0 mmol), [2-(dimethylamino)ethoxy]ethene (0.23 g, 2.0 mmol), palladium acetate (0.00673 g, 0.030 mmol), triphenylphosphine (0.0173 g, 0.066 mmol) triethylamine (0.202 g, 2.0 mmol) and 0.75 ml DMF.under nitrogen. The contents of the flask were irradiated for 7.00 min with an effect of 35 W. After cooling, the product mixture was diluted with 50 ml pentane, transferred to a separatory funnel and washed with 2×25 ml water. Additional extraction of the aqueous phases was performed with 25 ml pentane. The combined organic portions were then treated 5 times with 20 ml of 0.1 M HCl. The aqueous extracts were combined, poured into a flask containing excess NaOH (1.0 M) and was extracted with 2×50 ml pentane. The combined organic phases were dried (K2CO3) and concentrated by evaporation. The yield was 87% (yellow oil, trans/cis 1/1).

Aufarbeitung

  1. customThe contents of the flask were irradiated for 7.00 min with an effect of 35 W
  2. temperatureAfter cooling
  3. customtransferred to a separatory funnel
  4. washwashed with 2×25 ml water
  5. extractionAdditional extraction of the aqueous phases
  6. additionThe combined organic portions were then treated 5 times with 20 ml of 0.1 M HCl
  7. additionpoured into a flask
  8. additioncontaining excess NaOH (1.0 M)
  9. extractionwas extracted with 2×50 ml pentane
  10. dry with materialThe combined organic phases were dried (K2CO3)
  11. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-270971c7c18d412cbbc9a60a2c91ba80
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136157

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