Dimethylformamide → 9-Benzyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 1057592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057592
[H-].[Na+].[CH3:3][N:4]([CH:6]=O)[CH3:5].[CH2:8]1[CH2:12][O:11][CH2:10][CH2:9]1.C(Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCCCCC>[CH2:6]([N:4]1[C:3]2[CH2:12][CH2:8][CH2:9][C:10](=[O:11])[C:17]=2[C:16]2[C:5]1=[CH:18][CH:19]=[CH:14][CH:15]=2)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl Bromide2×HCID 8028TetrahydrofuranHCID 24758Sodium hydride

Produkt 1

HCID 27279169-Benzyl-1,2,3,9-tetrahydro-4H-carbazol-4-oneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in oil; 0.207 g, 5.18 mmol) is washed three times with hexane. DMF (3 mL) is added, followed by 36B added in portions. A moderate exotherm ensued; THF (3 mL) is added. After ten minutes benzyl bromide (1.047 g, 6.12 mmol) is added. After stirring for 4 h, an additional 0.1 g of benzyl bromide is added. The mixture is stirred overnight and then the solvents are removed; the residue is partitioned between CH2C2 and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate. Chromatography on silica gel (150 mL) using CH3OH—CH2Cl2 (1/99) as eluent, followed by re-chromatography of mixed fractions using EtOAc-hexane (30/70), gave 1.023 g (79%) of the title compound; mp 157.0-157.5° C.; IR (drift) 2940, 1636, 1610, 1530, 1484, 1464, 1445, 1399, 1357, 1187, 1133, 749, 742, 731, 698 cm−1; 1H NMR (CDCl3) δ2.23, 2.60, 2.88, 5.34, 7.03, 7.2-7.3, 8.30. Anal. Calcd for C19H17NO: C, 82.88; H, 6.22; N, 5.09. Found: C, 82.51; H, 6.21; N, 5.13.

Aufarbeitung

  1. additionadded in portions
  2. stirringThe mixture is stirred overnight
  3. customthe solvents are removed
  4. customthe residue is partitioned between CH2C2 and aq. sodium bicarbonate
  5. dry with materialThe organic layers are dried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-773a6d17802c4c259224c5c87064aea0
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514968B1

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