Sodium borohydride → HCID 21866194, compound

HRID 857738Notes

Reaction equation

HRID 857738 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[BH4-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21866208HCID 21866208, compound

Product 1

HCID 21866194HCID 21866194, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 2-pyrazin-2-ylbenzaldehyde (9.9 mmol from the previous step) in absolute MeOH (100 mL) at 0° C. was added sodium borohydride (420 mg, 11.1 mmol) in portions. The mixture was allowed to warm to room temperature and stirred under N2 atmosphere for 2 h. The solvent was removed in vacuo and the residue was treated with saturated aqueous NH4Cl. The mixture was extracted twice with EtOAc and the combined organic extracts were washed successively with H2O and brine, dried (MgSO4), filtered and concentrated to give a brown oil. Silica gel chromatography (70% EtOAc-hexanes) afforded the title compound as a pale red-brown oil. 1H NMR (400 MHz, CDCl3): δ 8.96 (s, 1 H), 8.65–8.61 (m, 2 H), 7.62–7.46 (m, 4 H), 5.18 (t, J=7.2 Hz, 1 H), 4.49 (d, J=7.2 Hz, 2 H). LCMS (M+H): 186.9.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was treated with saturated aqueous NH4Cl
  3. extractionThe mixture was extracted twice with EtOAc
  4. washthe combined organic extracts were washed successively with H2O and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil

Sources & evidence

ORD record
ord-f529e96fe9bd4297a993c66bee20e4ff
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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