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

HRID 551304

Reaktionsgleichung

Reaktionsgleichung von HRID 551304
[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 (LHMS) (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, 3H) 2.19 (m, 1H) 2.35 (m, 2H) 2.47 (m, 1H) 3.04 (d, J=16.11 Hz, 1H) 3.15 (d, J=16.11 Hz, 1H) 6.25 (s, 1H) 7.13 (t, J=8.55 Hz, 2H) 7.47 (m, 6H) 7.55 (s, 1H) 7.87 (m, 1H) 8.00 (m, 3H) 8.39 (s, 1H) 8.43 (s, 1H); 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-2a68b8636ad94b1abc70f3e190d5fcab
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947726B2

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