Dimethylformamide → HCID 19368852, compound

HRID 1534691Notes

Reaction equation

HRID 1534691 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH:4]=[CH2:5].C([Li])CCC.[C:18](=O)=[O:19].CC(C)=O.CN(C)C=O>O1CCCC1.CCCCCC.O>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:18]=[O:19])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 15419321HCID 15419321, compoundHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 19368852HCID 19368852, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1.13 g of 4-(4-pentenyl)-bromobenzene in 20 ml of tetrahydrofuran wa added dropwise 4 ml of 1.5 M n-butyl lithium in n-hexane with dry-ice - acetone cooling, and the mixture was stirred for 15 minutes. To the reaction mixture was added 0.58 ml of dimethylformamide and stirred for an hour. Then the reaction mixture, after addition of 50 ml of water, was extracted with ether. The organic layer was washed with water and dried. Evaporation of the solvent under reduced pressure gave 850 mg of 4-(4-pentenyl)benzaldehyde.

Workup

  1. stirringstirred for an hour
  2. extractionwas extracted with ether
  3. washThe organic layer was washed with water
  4. customdried
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-94cb281a4a3444da8c1f396c7d9fa62c
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

Loading…