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Cerium(III) chloride → HCID 178459058, Verbindung

HRID 76270
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 76270
[Cl-].[Ce+3].[Cl-].[Cl-].[C:5]([N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:19])[CH3:18])/[C:11](=[N:20]/[C:21](=[O:33])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:23]=2[F:32])/[S:10]1)([CH3:8])([CH3:7])[CH3:6].[CH3:34][Mg]Br>C1COCC1>[C:5]([N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])([CH3:34])[CH3:18])/[C:11](=[N:20]/[C:21](=[O:33])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[C:23]=2[F:32])/[S:10]1)([CH3:6])([CH3:7])[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24636Cerium(III) chlorideHCID 178418573HCID 178418573, VerbindungHCID 178467761HCID 178467761, Verbindung

Produkt 1

HCID 178459058HCID 178459058, VerbindungAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To the suspension of cerium(III) chloride (86 mg, 0.35 mmol) in THF (3 mL) was added the product from Example 77 (100 mg, 0.23 mmol) in THF (0.5 mL). The mixture was stirred at rt for 1 hr. The above mixture was cooled to −40° C. and methylmagnesium bromide (41.6 mg, 0.348 mmol) was added dropwise. The reaction was stirred for 40 min at −40° C., quenched with saturated aqueous NH4Cl and extracted with CH2Cl2 (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 57 mg (55%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.23 (s, 6 H) 1.57-1.61 (m, 2 H) 1.68 (s, 9 H) 1.74 (s, 1 H) 1.81-1.89 (m, 2 H) 2.88 (t, J=7.63 Hz, 2 H) 7.30 (t, J=7.93 Hz, 1 H) 7.69 (t, J=6.41 Hz, 1 H) 8.01-8.04 (m, 1 H) 8.39 (td, J=7.93, 1.53 Hz, 1 H); MS (DCI/NH4+) m/z 447 (M+H)+.

Aufarbeitung

  1. temperatureThe above mixture was cooled to −40° C.
  2. stirringThe reaction was stirred for 40 min at −40° C.
  3. customquenched with saturated aqueous NH4Cl
  4. extractionextracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cd573958a6994c6b84dedfa0b816280c
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835475B2

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