Sodium borohydride → [6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol

HRID 2194897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194897
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[C:15]([C:16](OC)=[O:17])=[CH:14][N:13]=1.[BH4-].[Na+]>CO.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]=[CH:14][C:15]([CH2:16][OH:17])=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 67447798Methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate

Produkt 1

HCID 67448255[6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate (1 eq.) from step 1, in MeOH (0.14M) was added portion wise sodium borohydride (9.3 eq.). The mixture was stirred at 65° C. for 12 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/EtOAc 20% afforded the desired compound as an oil.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel
  9. washeluting with Hex/EtOAc 20%

Quellen und Nachweise

ORD-Eintrag
ord-709134f9f9724bd6b5db0381c8e33ee6
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334308B2

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