3-(Pyrazin-2-yl)benzaldehyde → (3-(Pyrazin-2-YL)phenyl)methanol

HRID 41588Notes

Reaction equation

HRID 41588 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11].[BH4-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 38624353-(Pyrazin-2-yl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 53425549(3-(Pyrazin-2-YL)phenyl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-(pyrazin-2-yl)benzaldehyde [376637-85-3] (200 mg, 1.09 mmol) in methanol (5 mL), NaBH4 (82 mg, 2.17 mmol) was added at 0° C. and stirred for 10 min. Then the mixture was allowed to warm to rt and stirred for 3 h. The mixture was concentrated under reduced pressure at 45° C., saturated aqueous NH4Cl solution was added and extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield the title compound as a liquid (200 mg, 99%). [LCMS RtE=0.20 min, [M+H]+=187.0; TLC Rf=0.26 (ethyl acetate/hexane 50:50)].

Workup

  1. stirringstirred for 3 h
  2. concentrationThe mixture was concentrated under reduced pressure at 45° C.
  3. additionsaturated aqueous NH4Cl solution was added
  4. extractionextracted with ethyl acetate (2×5 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aceea09280ce4553a021bcb1cc38473c
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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