Sodium Bicarbonate → 2-Thiophenemethanol, 5-(3-pyridinyl)-

HRID 1913364Notes

Reaction equation

HRID 1913364 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S: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[S:11][C:10]([CH2:12][OH:13])=[CH:9][CH:8]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 108994275-(Pyridin-3-yl)thiophene-2-carbaldehyde

Product 1

HCID 118163512-Thiophenemethanol, 5-(3-pyridinyl)-Yield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 13 (116 mg, 0.61 mmol) in CH3OH (5 mL) was added sodium borohydride (23 mg, 0.61 mmol) in one portion. The resultant solution was stirred at room temperature for 10 min, stopped by the addition of aqueous sodium bicarbonate (50:50 satd. soln./water, v:v) and the solvent was removed in vacuo. The residue was partitioned between water (50 mL) and EtOAc (50 mL). The organic layer was collected and the aqueous was extracted with EtOAc (2×50 mL). The combined organic extracts were dried (MgSO4) and the solvent was removed in vacuo to afford the title compound 44 (116 mg, 99% yield) as an off white solid: mp=89-90° C.; 1H NMR (CDCl3) δ 8.82 (m, 1H), 8.49 (m, 1H), 7.84 (m, 1H), 7.31 (m, 1H), 7.22 (d, J=4.1 Hz, 1H), 7.01 (d, J=4.1 Hz, 1H), 4.85 (s, 2H); LRMS (ESI) m/z calcd for C11H10NOS [M+H]+ 192. found 192; HRMS (ESI) m/z calcd for C10H10NOS [M+H]+ 192.0483. found 192.0476; HPLC>99% (tR=10.18 min, 55 (A):45 (B) 0.009 (C); tR=3.52 min, 55 (A):45 (B) 0.1 (C)).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between water (50 mL) and EtOAc (50 mL)
  3. customThe organic layer was collected
  4. extractionthe aqueous was extracted with EtOAc (2×50 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cbec47cc44834be7bf224460bb9bec3e
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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