Methanol → HCID 9884617, Verbindung

HRID 1057662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057662
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][C:23]#[N:24])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH2:24])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 887Methanol2×HCID 18671671[(9-Benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile

Produkt 1

HCID 9884617HCID 9884617, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of [(9-benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile (0.9 g, 2.6 mmol) in dry THF (50 mL) is added borane-methylsulfide complex (0.75 mL, 7.9 mmol). The mixture is heated at 40° C. overnight. Methanol is slowly added to mixture until addition of methanol did not evolve gas. The solvents are removed under reduced pressure. Methanol (50 mL) is added to the residue then removed under reduced pressure. Methanol (100 mL) and concentrated hydrochloric acid (3 mL) is added to the residue. The mixture is heated at 75° C. for 2.5 h. The mixture is neutralized with saturated potassium carbonate and partitioned between water and ethyl acetate. The layers are separated and the organic layer washed twice with brine. The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography, silica gel (100 mL) using CH2Cl2: CH3OH (95:5) as eluent gave 0.52 g (58%) of the title compound; 1H NMR (DMSO-d6) δ2.48, 3.8, 4.12, 5.59, 6.69, 6.8, 7.14, 7.2, 8.03; Anal. Calcd for C22H22N2O2: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.00; H, 6.54; N, 7.92.

Aufarbeitung

  1. additionis added borane-methylsulfide complex (0.75 mL, 7.9 mmol)
  2. customThe solvents are removed under reduced pressure
  3. additionMethanol (50 mL) is added to the residue
  4. customthen removed under reduced pressure
  5. additionMethanol (100 mL) and concentrated hydrochloric acid (3 mL) is added to the residue
  6. temperatureThe mixture is heated at 75° C. for 2.5 h
  7. custompartitioned between water and ethyl acetate
  8. customThe layers are separated
  9. washthe organic layer washed twice with brine
  10. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3fd934a8df21413d88b445482b5f48d5
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514968B1

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