Sodium borohydride → 3-(4-(2-Pyrazinyl)phenyl)prop-2-en-1-ol

HRID 2416565Notes

Reaction equation

HRID 2416565 reaction equation
[BH4-].[Na+].[N:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH:17]=[O:18])=[CH:11][CH:10]=2)[CH:4]=1>C(O)C>[N:6]1[CH:7]=[CH:8][N:3]=[CH:4][C:5]=1[C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[CH:16][CH2:17][OH:18])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22631067(2E)-3-[4-(3-pyrazinyl)phenyl]-2-propenal

Product 1

HCID 697135193-(4-(2-Pyrazinyl)phenyl)prop-2-en-1-olYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (90 mg, 2.38 mmol) was added to a suspension of (2E)-3-[4-(3-pyrazinyl)phenyl]-2-propenal (400 mg, 1.90 mmol, prepared as described in Reference Example 18) in ethanol (5 mL) maintained in a room temperature water bath. After 20 min, the reaction was quenched with water (10 mL), allowed to stir for 10 min, and then concentrated to remove the ethanol. The solids were removed by filtration, washed with water, and dried in vacuo to provide 360 mg (89%) of the title compound. MS 213 (M+H)+.

Workup

  1. customthe reaction was quenched with water (10 mL)
  2. concentrationconcentrated
  3. customto remove the ethanol
  4. customThe solids were removed by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-25886b0cbfaa43a78a47da7d28b3a119
Source dataset
uspto-grants-2004_11
Patent number
US06825172B2

Reaction notes

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