Ethyl 2-ethylnicotinate → (2-Ethylpyridin-3-yl)methanol

HRID 2240374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240374
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[CH2:17][CH3:18])C>O1CCCC1>[CH2:17]([C:12]1[C:11]([CH2:10][OH:9])=[CH:16][CH:15]=[CH:14][N:13]=1)[CH3:18]

Komponenten

4

Edukt 2

HCID 14580149Ethyl 2-ethylnicotinateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 19690951(2-Ethylpyridin-3-yl)methanolAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of LiAlH4 (0.83 g, 21.76 mmol) in tetrahydrofuran (50 ml) was added drop wise a solution of 2-ethyl-nicotinic acid ethyl ester (Breitmaier et al, Tetrahedron, 26, 1970, 5907-5910) (3 g, 16.74 mmol) in tetrahydrofuran (25 ml) at −50° C. After addition, the temperature was slowly allowed to increase to 0° C. After 3 h, the reaction was quenched with saturated NH4Cl, filtered and washed with 1M NaHCO3 (50 ml). The aqueous layer was extracted with ethyl acetate (3×50 ml). Combined organic extract were dried (Na2SO4), filtered and concentrated to yield 1.6 g (54%) of product as a yellowish liquid. MS (ESI+) m/z 138 (M+H)+;

Aufarbeitung

  1. additionAfter addition
  2. customthe reaction was quenched with saturated NH4Cl
  3. filtrationfiltered
  4. washwashed with 1M NaHCO3 (50 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
  6. extractionCombined organic extract
  7. dry with materialwere dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-929e9d057f224b28a500063eedb00470
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723367B2

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