Sodium Bicarbonate → (5-(Pyridin-3-yl)furan-2-yl)methanol

HRID 1913365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913365
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=2)[CH:2]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][C:10]([CH2:12][OH:13])=[CH:9][CH:8]=2)[CH:2]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 122152605-(Pyridin-3-yl)furan-2-carbaldehyde

Produkt 1

HCID 11446630(5-(Pyridin-3-yl)furan-2-yl)methanolAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a slurry of 23 (54 mg, 0.31 mmol) in CH3OH (5 mL) was added sodium borohydride (12 mg, 0.31 mmol) in one portion and the resultant solution was stirred at room temperature for 10 min. The reaction was stopped by the addition of aqueous sodium bicarbonate (50:50 satd. soln./water, v:v) and the CH3OH was removed in vacuo. The residue was partitioned between water (20 mL) and ether (20 mL), the organic layer was collected and the aqueous fraction was re-extracted with ether (2×20 mL). The combined organic portions were washed with water (20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound 45 (50 mg, 92% yield) as an off white solid: mp=119-120° C.; 1H NMR (CDCl3, 500 MHz) δ 8.88 (s, 1H), 8.42 (m, 1H), 7.88 (m, 1H), 7.27, (m, 1H), 6.65 (d, J=3.1 Hz, 1H), 6.38 (d, J=3.1 Hz, 1H), 4.66 (s, 2H); LRMS (ESI) m/z calcd for C10H10NO2 [M+H]+ 176. found 176; HRMS (ESI) m/z calcd for C10H10NO2[M+H]+ 176.0712. found 176.0694; HPLC>98% (tR=4.60 min, 55 (A):45 (B): 0.032 (C); tR=3.64 min, 55 (A):45 (B): 0.1 (C)).

Aufarbeitung

  1. customthe CH3OH was removed in vacuo
  2. customThe residue was partitioned between water (20 mL) and ether (20 mL)
  3. customthe organic layer was collected
  4. extractionthe aqueous fraction was re-extracted with ether (2×20 mL)
  5. washThe combined organic portions were washed with water (20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b84334c03dd744e4886b0d2ace7dff71
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609708B2

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