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Tetrabutylammonium Fluoride → 2-Cyano-N-cyclopropyl-N-(2,3-dichlorobenzyl)-3-[4-(3-hydroxypropyl)phenyl]-2-methylpropanamide

HRID 561850
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561850
[Si]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([C:36]#[N:37])([CH3:35])[C:20]([N:22]([CH:32]2[CH2:34][CH2:33]2)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=2[Cl:31])=[O:21])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:36]([C:19]([CH3:35])([CH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[CH:17][CH:16]=1)[C:20]([N:22]([CH:32]1[CH2:34][CH2:33]1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[Cl:31])=[O:21])#[N:37]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 667608183-[4-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)phenyl]-2-cyano-N-cyclopropyl-N-(2,3-dichlorobenzyl)-2-methylpropanamide

Produkt 1

HCID 667613132-Cyano-N-cyclopropyl-N-(2,3-dichlorobenzyl)-3-[4-(3-hydroxypropyl)phenyl]-2-methylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-[4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)phenyl]-2-cyano-N-cyclopropyl-N-(2,3-dichlorobenzyl)-2-methylpropanamide from the previous step (1 eq.) in THF (0.2 M) was added tetrabutylammonium fluoride (1.0 M THF solution, 8 eq.). The resulting reaction mixture was stirred at RT for 4 h. After quenching the reaction with 10% aq. HCl, the mixture was extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a pale yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customAfter quenching
  3. customthe reaction with 10% aq. HCl
  4. extractionthe mixture was extracted with ether
  5. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customConcentration of the filtrate in vacuo afforded a pale yellow oil
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-fdcc077b0b5e40f7a665597ff1da71ef
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063105B2

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