Dimethylformamide → HCID 12540231, compound

HRID 2255395Notes

Reaction equation

HRID 2255395 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:11][C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[C:9]#[N:10])=[CH:4][CH:3]=1.C1COCC1.CN(C=O)C.[BH4-].[Na+]>O.C(Cl)Cl.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 324048(2Z)-2-(4-chlorophenyl)-3-(2-furyl)-2-propenenitrileHCID 4311764Sodium borohydride

Product 1

HCID 12540231HCID 12540231, compoundYield 90.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a flask under a nitrogen atmosphere was added 9.24 g. (0.04 mole) of 2-(4-chlorophenyl)-3-(2-furyl)acrylonitrile in 55 ml. of a 10 to 1 mixture of THF and DMF. While stirring at room temperature, 1.44 g. (0.04 mole) of sodium borohydride in 25 ml. of ethanol was added and the resulting mixture stirred for an additional 18 hours. A mixture of 175 ml. of 6 to 1 methylene chloride and water was added to the reaction while stirring at room temperature. The methylene chloride solution was washed with 10% aqueous hydrochloric acid, dried, and concentrated to give 8.24 g. (90.4% yield) of 2-(4-chlorophenyl)-3-(2-furyl)propionitrile as a thick oil.

Workup

  1. additionTo a flask under a nitrogen atmosphere was added 9.24 g
  2. stirringthe resulting mixture stirred for an additional 18 hours
  3. additionA mixture of 175 ml
  4. stirringwhile stirring at room temperature
  5. washThe methylene chloride solution was washed with 10% aqueous hydrochloric acid
  6. customdried
  7. concentrationconcentrated
  8. customto give 8.24 g

Sources & evidence

ORD record
ord-929eabafbfd04a4c94c34e5904acf0e7
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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