Dimethylacetamide → 5-(4-Chlorobenzyl)-2,2-dimethylcyclopentanone

HRID 1500147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500147
COC([C:5]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]1=[O:12])=O.CN(C)C(=O)C.Cl.N1C=CC=CC=1.O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH:5]2[C:6](=[O:12])[C:7]([CH3:11])([CH3:10])[CH2:8][CH2:9]2)=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 31374DimethylacetamideHCID 10176127Pyridinium chloride2×HCID 11449298HCID 11449298, VerbindungHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 114248965-(4-Chlorobenzyl)-2,2-dimethylcyclopentanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

In 1-(4-chlorobenzyl)-3,3-dimethyl-2-oxocyclopentane carboxylic acid methyl ester (1.5 g, 0.00509 mol), N,N-dimethylacetamide (1.5 mL) and pyridine hydrochloride (0.706 g, 0.00509×1.2 mol) were added and stirred at 155° C. for 4 hours. In the reaction liquid, pyridine hydrochloride (0.177 g, 0.00509×0.3 mol) was added and further stirred at 155° C. for another 6 hours. In the reaction liquid, toluene and saturated sodium bicarbonate water were added, and the mixture was partitioned. After extracting the aqueous layer using toluene, the organic layer was dried using anhydrous sodium sulfate and concentrated. Thereafter, the dried and concentrated product was purified using a silica gel column, and a target product was obtained.

Aufarbeitung

  1. additionwas added
  2. stirringfurther stirred at 155° C. for another 6 hours
  3. additionwere added
  4. customthe mixture was partitioned
  5. extractionAfter extracting the aqueous layer
  6. customthe organic layer was dried
  7. concentrationconcentrated
  8. customThereafter, the dried
  9. customconcentrated product was purified
  10. customa target product was obtained

Quellen und Nachweise

ORD-Eintrag
ord-f4a57ef729f04f1dba62e08ba995becf
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206106B2

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