Diethyl Ether → (2,10-Dihydro-1H-fluoreno[2,1-b]furan-10-ylidene)acetonitrile

HRID 617418Notes

Reaction equation

HRID 617418 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH2:14]1[CH2:18][O:17][C:16]2[CH:19]=[CH:20][C:21]3[C:22]4[C:27]([C:28](=O)[C:29]=3[C:15]1=2)=[CH:26][CH:25]=[CH:24][CH:23]=4.CCOCC>C1COCC1.[Cl-].[Na+].O>[CH2:14]1[CH2:18][O:17][C:16]2[CH:19]=[CH:20][C:21]3[C:22]4[C:27]([C:28](=[CH:3][C:1]#[N:2])[C:29]=3[C:15]1=2)=[CH:26][CH:25]=[CH:24][CH:23]=4

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 218521842,10-dihydro-1H-fluoreno[2,1-b]furan-10-one

Product 1

HCID 67593602(2,10-Dihydro-1H-fluoreno[2,1-b]furan-10-ylidene)acetonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A magnetically stirred solution of diethyl cyanomethylphosphonate (0.502 g, 2.83 mmol) in anhydrous THF (150 mL) was treated with sodium hydride (60% in mineral oil, 0.113 g, 2.82 mmol) in portions. The resultant suspension was treated dropwise with 2,10-dihydro-1H-fluoreno[2,1-b]furan-10-one (0.525 g, 2.36 mmol) in THF (100 mL), stirred 12 h, poured over ice (100 g), and treated with brine (100 mL), and Et2O (150 mL). The layers were separated and the aqueous layer further extracted with fresh Et2O (2×150 mL). The combined organic extracts were washed with brine (200 mL), dried (K2CO3), filtered, and concentrated in vacuo.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer further extracted with fresh Et2O (2×150 mL)
  3. washThe combined organic extracts were washed with brine (200 mL)
  4. dry with materialdried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22e0d73f00484355926b7cc8eac6839b
Source dataset
uspto-grants-1999_09
Patent number
US05948817

Reaction notes

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