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Sodium borohydride → (5-((5,5-Dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methanol

HRID 709803
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 709803
[CH3:1][C:2]1([CH3:28])[O:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[C:10]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=3[F:27])=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14](OC)=[O:15])[CH2:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:28])[O:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:18]=[C:13]([CH2:14][OH:15])[CH:12]=[N:11][C:10]=2[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=2[F:27])[CH2:3]1
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Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 117760190Methyl 5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate

Produkt 1

HCID 117760261(5-((5,5-Dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methanolAusbeute 107,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of methyl 5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate (700 mg) in methanol (10 mL) was cooled to 0° C., and sodium tetrahydroborate (342 mg) was slowly added by small portions. The reaction mixture was stirred at 60° C. for 4 hr. The solvent was evaporated under reduced pressure, saturated brine was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (700 mg) as a pale-yellow oil. This compound was used for the next step without further purification.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure, saturated brine
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6ad868598e3947d4952b9a04474df88d
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181186B2

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