Sodium Bicarbonate → (5-pyridin-3-ylfuran-2-yl)methanol

HRID 1913365Notes

Reaction equation

HRID 1913365 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 11446630(5-pyridin-3-ylfuran-2-yl)methanolYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)).

Workup

  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

Sources & evidence

ORD record
ord-b84334c03dd744e4886b0d2ace7dff71
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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