Tetrahydrofuran → HCID 19966195, Verbindung

HRID 1734862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734862
[CH:1]1([CH2:7][Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[C:15]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]=[O:28])=[CH:21][C:20]=1[NH:29][C:30](=[O:46])[CH2:31][CH:32]1[C:45]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[O:39][C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)([CH3:18])([CH3:17])[CH3:16].[Cl-].[NH4+]>C(OCC)C>[C:15]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]([OH:28])[CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:21][C:20]=1[NH:29][C:30](=[O:46])[CH2:31][CH:32]1[C:45]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[O:39][C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)([CH3:18])([CH3:16])[CH3:17]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 19966225HCID 19966225, VerbindungHCID 178419664HCID 178419664, Verbindung

Produkt 1

HCID 19966195HCID 19966195, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

0.18 ml of a 1M solution of cyclohexylmethylmagnesium bromide in diethyl ether was added to 2 ml of tetrahydrofuran, and the mixture was cooled to -78° C. 2 ml of a tetrahydrofuran solution containing 50 mg (0.12 mmol) of N-[2-t-butyl-5-(3-oxopropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 19) was then added dropwise to this solution, over a period of 5 minutes. The mixture was then stirred for 40 minutes at this temperature, after which the temperature was allowed to return gradually to 0° C. The reaction was then stopped by the addition of a saturated aqueous solution of ammonium chloride. Diethyl ether was added, which caused the title compound to be distributed between the organic solvent and water. The organic layer was separated and washed with water, after which the solvent was removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 10 g of silica gel. Elution with a 100:15 by volume mixture of methylene chloride and ethyl acetate afforded 41 mg (yield 67%) of the title compound as crystals, melting at 145°-146° C. (after recrystallization from a mixture of methylene chloride and diethyl ether).

Aufarbeitung

  1. additionwas then added dropwise to this solution, over a period of 5 minutes
  2. customto return gradually to 0° C

Quellen und Nachweise

ORD-Eintrag
ord-6063bddb5dce4a6885b3ed1c3e453d42
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534529

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