Sodium borohydride → HCID 137329845, compound

HRID 2228406Notes

Reaction equation

HRID 2228406 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([SiH:12]([CH3:14])[CH3:13])[C:7]([CH:10]=[O:11])=[N:8][CH:9]=1)[CH:2]=[CH2:3].[BH4-].[Na+]>CCO>[CH2:1]([C:4]1[CH:5]=[C:6]([SiH:12]([CH3:14])[CH3:13])[C:7]([CH2:10][OH:11])=[N:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 137329844HCID 137329844, compound

Product 1

HCID 137329845HCID 137329845, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-allyldimethylsilyl-2-pyridinecarboxaldehyde (8 Scheme 27, 3.1 g, 15 mmol) in EtOH (80 mL) was added sodium borohydride (1.1 g, 30 mmol) portion-wise for 10 min at room temperature. After further stirring for 30 min, excess sodium borohydride was quenched by slow addition of acetone (5 mL) to the reaction mixture. The solvent was evaporated and the residue was extracted with ethyl acetate/brine. The organic layer was dried (Na2SO4) and concentrated to afford an oil (2.7 g, 87%); 1H NMR (300 MHz, CDCl3) δ 0.27 (s, 6 H), 1.72 (dt, J=6.75, 1.05 Hz, 2 H), 4.74 (s, 2 H), 4.80 (dd, J=3.00, 1.20 Hz, 1 H), 4.48 (d, J=1.20 Hz, 1 H), 5.36 (bs, OH, 1 H), 5.69 (ddt, J=14.70, 9.30, 7.80 Hz, 1 H), 7.33 (d, J=7.80 Hz, 1 H), 7.76 (d, J=7.80 Hz, 1 H), 8.54 (s, 1 H), 13C NMR (75 MHz, CDCl3) −3.4 (2C), 23.5, 64.6 114.3, 120.6, 131.9, 133.9, 142.6, 153.0, 160.8. HRMS (EI) calcd for C11H17NOSi 207.1079, found 206.0999.

Workup

  1. customexcess sodium borohydride was quenched by slow addition of acetone (5 mL) to the reaction mixture
  2. customThe solvent was evaporated
  3. extractionthe residue was extracted with ethyl acetate/brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8332a2747ccc42d9924280d1ee5b7aff
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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