Sodium borohydride → HCID 67777887, compound

HRID 44149Notes

Reaction equation

HRID 44149 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6](/[CH:11]=[C:12](\[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)/[C:13]#[N:14])[CH:7]=[CH:8][C:9]=1[CH3:10]>CCO>[CH3:3][C:4]1[CH:5]=[C:6]([CH2:11][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[C:13]#[N:14])[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67778514(2E)-3-(3,4-dimethylphenyl)-2-(3-methoxyphenyl)acrylonitrile

Product 1

HCID 67777887HCID 67777887, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

NaBH4 (1.8 g, 47 mmol) was added slowly to the solution of (2E)-3-(3,4-dimethylphenyl)-2-(3-methoxyphenyl)acrylonitrile (6.17 g, 23.5 mmol) in EtOH (100 mL) under argon. The mixture was stirred at 70° C. for 16 h. The solution was cooled to room temperature and quenched with water. The reaction mixture was diluted with 100 mL water and acidified with 6M HCl (aq.). After extraction with ether (3×100 mL), the combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated to get 3-(3,4-dimethylphenyl)-2-(3-methoxyphenyl)propanenitrile as a white solid (6 g, 96%).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customquenched with water
  3. additionThe reaction mixture was diluted with 100 mL water
  4. extractionAfter extraction with ether (3×100 mL)
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1c0d8e6efc394d699f83f3a930779f07
Source dataset
uspto-grants-2013_09
Patent number
US08541397B2

Reaction notes

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