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Hydrochloric Acid → HCID 12540260, Verbindung

HRID 1413235
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1413235
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:14]1([C:19]2([CH3:39])[CH2:27][C:26]3[C:21](=[C:22]([Cl:37])[C:23]([Cl:36])=[C:24](OS(C(F)(F)F)(=O)=O)[CH:25]=3)[C:20]2=[O:38])[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>CN(C)C=O.C(Cl)Cl>[CH:14]1([C:19]2([CH3:39])[CH2:27][C:26]3[C:21](=[C:22]([Cl:37])[C:23]([Cl:36])=[C:24]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH:25]=3)[C:20]2=[O:38])[CH2:15][CH2:16][CH2:17][CH2:18]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 125402562-Cyclopentyl-6,7-dichloro-2-methyl-5-trifluoromethylsulfonyloxy-1-indanone

Produkt 1

HCID 12540260HCID 12540260, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
3×
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of sodium hydride (2.88 g., 120 mmole) in dry dimethylformamide (20 ml), under dry nitrogen and cooled in an ice-bath is added dropwise, a solution of diethyl malonate (19.2 g., 120 mmole) in dimethylformamide (30 ml). The mixture is stirred for one hour in the ice-bath and another hour at room temperature, then is cooled in the ice-bath again and 2-cyclopentyl-6,7-dichloro-2-methyl-5-trifluoromethylsulfonyloxy-1-indanone (12.93 g., 30 mmole) in dimethylformamide (25 ml) is added dropwise over 1-1/2 hours. The mixture is stirred at room temperature overnight and then poured into a mixture of ice-water (750 ml), methylene chloride (200 ml) and 6 N hydrochloric acid (20 ml). The methylene chloride layer is separated and the aqueous layer extracted with methylene chloride (50 ml). The combined extract is washed with water (500 ml), dried (MgSO4) and evaporated under vacuum, finally at 70°/0.05 Torr, to give an oil (18.28 g.). This is purified by chromatography on Merck silica gel (1.04 Kg) using 1,1,1-trichloroethane as the solvent. The product is accompanied by some diethyl malonate which is removed at 125°/0.05 Torr to give a viscous oil, 10.25 g. (77%),

Aufarbeitung

  1. temperatureunder dry nitrogen and cooled in an ice-bath
  2. additionis added dropwise
  3. customThe methylene chloride layer is separated
  4. extractionthe aqueous layer extracted with methylene chloride (50 ml)
  5. extractionThe combined extract
  6. washis washed with water (500 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated under vacuum, finally at 70°/0.05 Torr
  9. customto give an oil (18.28 g.)
  10. customThis is purified by chromatography on Merck silica gel (1.04 Kg)
  11. customis removed at 125°/0.05 Torr
  12. customto give a viscous oil, 10.25 g

Quellen und Nachweise

ORD-Eintrag
ord-e43b951722024e148771017bc90dd902
Quelldatensatz
uspto-grants-1981_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04249021

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