6-Methyl-5-nitropyridine-2-carbaldehyde → (6-Methyl-5-nitropyridin-2-yl)methanol

HRID 1811589

Reaktionsgleichung

Reaktionsgleichung von HRID 1811589
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Komponenten

4

Edukt 2

HCID 30151966-Methyl-5-nitropyridine-2-carbaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 24776197(6-Methyl-5-nitropyridin-2-yl)methanolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 6-methyl-5-nitropicolinaldehyde (50 g, 329 mmol) in ethanol (200 mL) was cooled to 10° C. and sodium borohydride (5.9 g, 157 mmol) was added portion-wise. The solution was allowed to stir for one half hour, the ethanol was removed and the residue partitioned between ethyl Acetate and water, the organic phase washed with brine, and dried with magnesium sulfate and stripped. The residue was purified by column chromatography (10-40% ethyl acetate/hexanes) to give (6-methyl-5-nitropyridin-2-yl)methanol (12 g, 91%), a pale white solid. 1HNMR (CDCl3, 400 MHz) δ 2.89 (s, 3H), 3.55 (t, J=5.05, 1H), 4.83 (d, J=4.55, 2H), 7.31 (d, J=8.34, 1H), 8.31 (d, J=8.34, 1H); Exact mass calculated for C7H8N2O3: 168.05. found: 169.10 MS m/z (MH+).

Aufarbeitung

  1. customthe ethanol was removed
  2. customthe residue partitioned between ethyl Acetate and water
  3. washthe organic phase washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customThe residue was purified by column chromatography (10-40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-933358bb108e42e68b5a6307b3eae3f8
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362248B2

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