Hexane → Benzofuran-3-acetonitrile

HRID 330288

Reaction equation

HRID 330288 reaction equation
CCCCCC.[H-].[Na+].[C:9]([CH2:11]P(=O)(OCC)OCC)#[N:10].[O:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=O)[CH2:21]1>C1COCC1.O>[O:20]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]([CH2:11][C:9]#[N:10])=[CH:21]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 23556CoumaranoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 2769401Benzofuran-3-acetonitrileYield 101%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of hexane washed sodium hydride (2.21 g, 0.046 mol, 50%/mineral oil) in THF (125 mL), was added diethyl cyanomethylphosphonate (8.15 g, 0.046 mol) dropwise. The reaction was stirred at room temperature for 1/2 hour, 3-coumaranone (sublimed) (5.6 g, 0.042 mol) in THF (100 mL) was added dropwise at 0° C., and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with water (300 mL), and extracted with ether (800 mL). The extracts were washed with brine (2×100 mL), dried (MgSO4), and concentrated to yield 6.67 g (100%) of the product as an off-white solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with ether (800 mL)
  3. washThe extracts were washed with brine (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b3c4eebd609749fc9e0e82105e841106
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Linked notes

Loading…