Tetrahydrofuran → 6-Anthracen-9-ylmethylene-1-(4-fluoro-phenyl)4a-methyl-1,4,4a,6,7,8-hexahydro-benzo[f]indazol-5-one

HRID 2307484

Reaktionsgleichung

Reaktionsgleichung von HRID 2307484
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[C:14]4CCCC(C=O)[C:13]4([CH3:23])[CH2:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH:24]1[C:37]2[C:28](=[CH:29][C:30]3[C:35]([C:36]=2[CH:38]=O)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=[CH:26][CH:25]=1.[CH2:40]1[CH2:44][O:43][CH2:42][CH2:41]1>>[CH:34]1[C:35]2[C:30](=[CH:29][C:28]3[C:37]([C:36]=2[CH:38]=[C:40]2[C:44](=[O:43])[C:13]4([CH3:12])[CH2:23][C:11]5[CH:10]=[N:9][N:8]([C:5]6[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=6)[C:16]=5[CH:15]=[C:14]4[CH2:42][CH2:41]2)=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:31]=[CH:32][CH:33]=1

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 695049-AnthracenecarboxaldehydeHCID 226059711-(4-Fluoro-phenyl)4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde

Produkt 1

HCID 865896206-Anthracen-9-ylmethylene-1-(4-fluoro-phenyl)4a-methyl-1,4,4a,6,7,8-hexahydro-benzo[f]indazol-5-oneAusbeute 78 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a 100 mL round bottom flask, aldehyde (207) (100 mg, 0.337 mmol) and anthracene-9-carboxaldehyde (349 mg, 1.69 mmol) were dissolved in 10 mL THF and cooled to 0° C. Lithium hexamethyldisilylamide (LHMDS) (370 μL, 0.370 mmol) was added dropwise, and the solution was stirred at room temperature for 16 hours. The reaction was quenched with 5 mL of saturated aqueous ammonium chloride. The aqueous layer was extracted with ether (3×10 mL), and the pooled organic extracts were washed with brine (10 mL), dried (MgSO4) and then concentrated. Flash chromatography of the residue (0-25% EtOAc/hexanes) gave (269) (127.9 mg, 78%). 1H NMR (CDCl3) δ 1.45 (s, 3 H) 2.19 (m, 1 H) 2.35 (m, 2 H) 2.47 (m, 1 H) 3.04 (d, J=16.11 Hz, 1 H) 3.15 (d, J=16.11 Hz, 1 H) 6.25 (s, 1 H) 7.13 (t, J=8.55 Hz, 2 H) 7.47 (m, 6 H) 7.55 (s, 1 H) 7.87 (m, 1 H) 8.00 (m, 3 H) 8.39 (s, 1 H) 8.43 (s, 1 H); 13C NMR (CDCl3) 23.5, 27.2, 29.7, 30.2, 49.4, 110.4, 114.0, 115.9, 116.1, 125.0, 125.1, 125.2, 125.3, 125.5, 126.1, 127.5, 128.8, 128.9, 128.9, 129.0, 129.7, 131.1, 131.1, 135.5, 135.7, 135.7, 136.4, 138.5, 139.1, 145.2, 160.2, 162.6, 202.8.

Aufarbeitung

  1. customThe reaction was quenched with 5 mL of saturated aqueous ammonium chloride
  2. extractionThe aqueous layer was extracted with ether (3×10 mL)
  3. washthe pooled organic extracts were washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-47759a1c0c2c45f48b455b35754c3a4c
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831093B2

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