Water → 2-(5-Bromopyridin-3-yl)ethan-1-ol

HRID 1253928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253928
B#B.C1COCC1.[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16](O)=[O:17])[CH:12]=[N:13][CH:14]=1.O>C1COCC1.C(OCC)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][OH:17])[CH:12]=[N:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 28025392-(5-Bromopyridin-3-yl)acetic acidHCID 131714434Diborane tetrahydrofuran

Produkt 1

HCID 534036902-(5-Bromopyridin-3-yl)ethan-1-olAusbeute 23,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of Diborane-THF complex (1.0 M in THF, 7.5 mL, 7.5 mmol) was added dropwise to a solution of 5-bromo-3-pyridinylacetic acid (1080 mg, 5 mmol) in dry THF at 0° C. The resulting mixture was allowed to warm to room temperature. After 15 h, the reaction mixture was cooled to 0° C. and water (10 mL) was added dropwise. The reaction mixture was diluted with ethyl acetate (100 mL). The organic layer was separated, washed with brine, dried over Na2SO4. After filtration and concentration, the residue was purified by flash column and afforded of the title compound as colorless solid (241 mg). 1HNMR (CDCl3, 400.342 MHz) δ 2.89 (t, J=6 Hz, 2H), 3.92 (t, J=6 Hz, 3H), 7.99 (s, 1H), 8.46 (s, 1H), 8.60 (s, 1H).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by flash column

Quellen und Nachweise

ORD-Eintrag
ord-c1b90bd9127a4706905ad6980b1cac65
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455522B2

Notizen zur Reaktion

Wird geladen…