N,N,N',N'-Tetramethylethylenediamine → HCID 516472, Verbindung

HRID 2215673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215673
C([Li])CCC.CCCCCC.CN(CCN(C)C)C.[CH3:20][C:21]1[S:25][C:24]2[C:26](=O)[CH2:27][CH2:28][C:23]=2[CH:22]=1.[CH2:30]([N:32]1[C:41]2[C:36](=[CH:37][C:38]([CH:42]([CH3:44])[CH3:43])=[CH:39][CH:40]=2)[C:35](=[O:45])C=C1C1OC=CC=1)[CH3:31]>C1COCC1.[Cl-].[NH4+]>[CH2:30]([N:32]1[C:41]2[C:36](=[CH:37][C:38]([CH:42]([CH3:44])[CH3:43])=[CH:39][CH:40]=2)[C:35](=[O:45])[C:27]2[CH2:28][C:23]3[CH:22]=[C:21]([CH3:20])[S:25][C:24]=3[C:26]1=2)[CH3:31]

Komponenten

8

Edukt 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 516434HCID 516434, VerbindungHCID 12416658HCID 12416658, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 516472HCID 516472, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a 1.53M solution of n-butyl lithium in hexane (0.47 mL, 0.72 mmol) were added under argon atmosphere TMEDA (0.11 mL, 0.72 mmol) at room temperature and then 2-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (0.11 g, 0.72 mmol) in anhydrous THF dropwise with ice cooling and stirring. The reaction mixture was stirred at room temperature for 1 hour and ice-cooled again. To this was added dropwise a solution of 1-ethyl-6-isopropylisatoic anhydride (Example 6, step 1) (0.11 g, 0.48 mmol) in anhydrous THF. The reaction mixture was stirred at room temperature for 2 hours and diluted with saturated aqueous solution of ammonium chloride. The organic layer was concentrated to dryness and the residue was dissolved in ethyl acetate. This solution was washed with saturated sodium chloride solution, dried with sodium sulfate and evaporated again. The residue was subjected to silica gel-chromatography (chloroform: acetone=9:1) and crystallization from diethyl ether to give the title compound. 1H-NMR (CDCl3) δ 1.33 (6H, d, CH(CH3)2), 1.58 (3H, t, CH2CH3), 2.64 (3H, s, CH3), 3.10 (1H, septet, CH), 3,78 (2H, s, H-4), 4,49 (2H, q, NCH2), 6.97 (1H, s, H-3), 7.49 (1H, d, H-9), 7.56 (1H, dd, H-8), 8.45 (1H, d, H-6)

Aufarbeitung

  1. temperatureice-cooled again
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours
  3. concentrationThe organic layer was concentrated to dryness
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThis solution was washed with saturated sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. customevaporated again
  8. customThe residue was subjected to silica gel-chromatography (chloroform: acetone=9:1) and crystallization from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-abc130b95ee24d2c8322f1dbdb04d591
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109338B2

Notizen zur Reaktion

Wird geladen…