Hydrochloric Acid → N-[2-t-Butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 1734898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734898
CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](OCC)=[O:30])=[CH:23][C:22]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:20])([CH3:19])[CH3:18].Cl>O1CCCC1>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][OH:30])=[CH:23][C:22]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:20])([CH3:18])[CH3:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 19966227N-[2-t-butyl-5-(2-ethoxycarbonylethyl)phenyl]-2-(9H-xanthen-9-yl)acetamideHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 19966239N-[2-t-Butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

5.96 ml (5.96 mmol) of a 1.0M hexane solution of diisobutylaluminum hydride were added dropwise, over a period of 10 minutes, to 14 ml of a tetrahydrofuran solution containing 702 mg (1.49 mmol) of N-[2-t-butyl-5-(2-ethoxycarbonylethyl)phenyl]-2-(9H-xanthen-9-yl)-acetamide (prepared as described in Preparation 17) which had previously been cooled at -78° C. The mixture was stirred for 75 minutes at this temperature and then for 45 minutes at room temperature. At the end of this time, the reaction solution was poured into a mixture of dilute aqueous hydrochloric acid and ice, and was then extracted with diethyl ether. The organic extract was washed with water, and then the solvent was removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 30 g of silica gel. Elution with a 5:4 by-volume mixture of methylene chloride and ethyl acetate afforded 427 mg (yield 67%) of the title compound as crystals, melting at 185°-186° C. (after recrystallization from a mixture of methylene chloride and diethyl ether).

Aufarbeitung

  1. waitfor 45 minutes at room temperature
  2. extractionwas then extracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with water
  5. customthe solvent was removed by distillation under reduced pressure
  6. washElution with a 5:4
  7. additionby-volume mixture of methylene chloride and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5c6253687a624a249f7b5e5ecc09ddce
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534529

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