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Sodium borohydride → Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]Methanol

HRID 2104492
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2104492
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CCO>[C:1]1([CH:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:26])[F:27])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 11360909Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone

Produkt 1

HCID 11222693Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]MethanolAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (Example 1, 0.200 g, 0.53 mmol) was taken into EtOH (5 mL) and cooled to 0° C. where was added NaBH4 (0.020 g, 0.53 mmol). The ice bath was removed and the reaction was allowed to stir at room temperature overnight. The EtOH was removed and water was added to the resulting material, where it was extracted with methylene chloride, dried over sodium sulfate and concentrated. The product was purified via column chromatography using 15% ethyl acetate in hexane as the eluent to afford 0.194 g of desired product as a white solid. MS (ESI) m/z 380 ([M+H]+); Anal. Calcd for C23H16F3NO: C, 72.82; H, 4.25; N, 3.69. Found: C, 72.52; H, 4.20; N, 3.55.

Aufarbeitung

  1. customThe ice bath was removed
  2. customThe EtOH was removed
  3. additionwater was added to the resulting material, where it
  4. extractionwas extracted with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-18116b48dff241ee91639aa6ce758f13
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07576215B2

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