Sodium hydride → 2-(3,4-Dihydro-2H-4-chromenylidene)acetonitrile

HRID 394666Notes

Reaction equation

HRID 394666 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[O:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=O)[CH2:16][CH2:15]1>O1CCCC1>[O:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[CH:3][C:1]#[N:2])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68110ChromanoneHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 569848342-(3,4-Dihydro-2H-4-chromenylidene)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Diethyl cyanomethylphosphonate (1.15 eq.) is slowly added to a suspension of sodium hydride (1.15 eq.) in anhydrous tetrahydrofuran at 0° C. The reaction medium is stirred for 10 minutes at 0° C. and then cooled to −78° C. 4-Chromanone dissolved in tetrahydrofuran is added. The temperature is then returned slowly to 20-25° C. over 2 hours 30. After removal of the solvent, the compounds are extracted with ethyl acetate. The organic phase is washed with a large amount of a saturated solution of sodium chloride, concentrated and purified (Z/E mixture) on a silica column (AcOEt/PE 3/7).

Workup

  1. temperaturecooled to −78° C
  2. additionis added
  3. waitThe temperature is then returned slowly to 20-25° C. over 2 hours
  4. customAfter removal of the solvent
  5. extractionthe compounds are extracted with ethyl acetate
  6. washThe organic phase is washed with a large amount of a saturated solution of sodium chloride
  7. concentrationconcentrated
  8. custompurified (Z/E mixture) on a silica column (AcOEt/PE 3/7)

Sources & evidence

ORD record
ord-c9307b8241da4fa28b5d39e90dbd41bb
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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