Sodium borohydride → 2-Pyridinemethanol, 6-[(difluoromethoxy)methyl]-

HRID 876986

Reaktionsgleichung

Reaktionsgleichung von HRID 876986
[BH4-].[Na+].[F:3][CH:4]([F:18])[O:5][CH2:6][C:7]1[N:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[CH:9][CH:8]=1>CCO>[F:18][CH:4]([F:3])[O:5][CH2:6][C:7]1[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 66718372Ethyl 6-difluoromethoxymethylpyridine-2-carboxylate

Produkt 1

HCID 667184182-Pyridinemethanol, 6-[(difluoromethoxy)methyl]-Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

NaBH4 (377 mg, 9.96 mmol) was added to a solution of ethyl 6-difluoromethoxymethylpyridine-2-carboxylate (2.30 g, 9.96 mmol) in EtOH (50 mL) at 0° C., the mixture was warmed to 80° C. and stirred for 5 h. The mixture was cooled to 0° C., quenched with sat. aq. NH4Cl, concentrated in vacuo and partitioned between EtOAc and brine. The organic layer was separated, dried (MgSO4), filtered and evaporated to give the title compound (1.50 g, 80%) as a colorless oil; NMR δH (400 MHz, CDCl3) 7.73 (1H, t, J 8.0 Hz), 7.35 (1H, d, J 8.0 Hz), 7.19 (1H, d, J 8.0 Hz), 6.39 (1H, t, J 74.0 Hz), 5.02 (2H, s), 4.76 (2H, s); (M+H)+ 190.

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with sat. aq. NH4Cl
  3. concentrationconcentrated in vacuo
  4. custompartitioned between EtOAc and brine
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6cd9753ac33f4a8a962a097181733aaf
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987279B2

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