Sodium borohydride → (4-Bromopyridin-2-yl)methanol

HRID 1427777

Reaktionsgleichung

Reaktionsgleichung von HRID 1427777
[BH4-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][N:8]=1)=O>C(O)C>[Br:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:5][OH:4])[CH:12]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 12828947Methyl 4-bromopicolinate

Produkt 1

HCID 14761462(4-Bromopyridin-2-yl)methanolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (763 mg, 20.17 mmol) was added portionwise to a solution of 4-bromo-pyridine-2-carboxylic acid methyl ester (1.98 g, 9.166 mmol) in ethanol (50 mL) under nitrogen and the reaction mixture was stirred at room temperature for 18 hours. The reaction was quenched by the addition of acetone (10 mL) and the reaction was stirred for 15 minutes. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organics were collected, dried over anhydrous sodium sulfate and the solvent evaporated to afford the title compound (1.61 g, 94%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ3.4-3.5 (br s, 1H), 4.80 (s, 2H), 7.40 (dd, J=5.4, 1.8 Hz, 1H), 7.50 (br m, 1H), 8.39 (d, J=5.4 Hz, 1H). LCMS (m/z) 188/200 [M+H], Tr=1.55 min.

Aufarbeitung

  1. customThe reaction was quenched by the addition of acetone (10 mL)
  2. stirringthe reaction was stirred for 15 minutes
  3. customThe solvent was evaporated
  4. customthe residue partitioned between water and ethyl acetate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. customthe combined organics were collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f9f844d8869a417397a4a3dc41321010
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933015B2

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