Methylenechloride Hexane → 2-Isopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydro-8,8-dimethylquinoline

HRID 324883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 324883
[CH:1]([C:4]1[C:13]([C:14](OCC)=[O:15])=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:27])([CH3:26])[C:6]=2[N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(Cl)Cl.CCCCCC>C1COCC1>[CH:1]([C:4]1[C:13]([CH2:14][OH:15])=[C:12]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:27])([CH3:26])[C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 21226440Methylenechloride HexaneHCID 21226445Aluminium lithium hydrideHCID 220050562-Isopropyl-3-carboethoxy-4-(4-fluorophenyl)-5,6,7,8-tetrahydro-8,8-dimethylquinoline

Produkt 1

HCID 220050492-Isopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydro-8,8-dimethylquinolineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the intermediate obtained in Step B (1.32 g, 3.6 mmol) in THF (35 mL) was added lithium aluminum hydride (1 M/THF, 2 eq., 7.2 mL) dropwise. The reaction was refluxed for 1.5 hours and cooled to room temperature. Then the reaction was quenched with water and the THF was evaporated. The residue was partitioned between diethyl ether (150 mL) and water (100 mL). The organic layer was washed with brine (1×100 mL), dried with MgSO4, filtered, and concentrated to afford a solid. Flash chromatography (40% CH2Cl2/hexane) afforded the title compound as a white solid (808 mg, 2.5 mmol, 70%). 1H NMR (300 MHz, CDCl3): δ 7.13 (d, J=7.0 Hz, 4H), 4.36 (d, J=5.5 Hz, 2H), 3.42 (septet, J=6.6 Hz, 1H), 2.24 (t, J=5.5 Hz, 2H), 1.67 (m, 4H), 1.32 (m, 13H). FAB-MS: calculated for (C21H26FNO) 327, found 328 (M+H). mp 146-149° C. Rf=0.2 (50% CH2Cl2/hexane).

Aufarbeitung

  1. temperatureThe reaction was refluxed for 1.5 hours
  2. customThen the reaction was quenched with water
  3. customthe THF was evaporated
  4. customThe residue was partitioned between diethyl ether (150 mL) and water (100 mL)
  5. washThe organic layer was washed with brine (1×100 mL)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a solid

Quellen und Nachweise

ORD-Eintrag
ord-323622702e754381a1102e9f24019b74
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218431B1

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