Diethyl (cyanomethyl)phosphonate → 1-(Cyanomethyl)-3-(cyanomethylene)cyclobutanecarbonitrile

HRID 1966156Notes

Reaction equation

HRID 1966156 reaction equation
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[C:18]([CH2:20][C:21]1([C:26]#[N:27])[CH2:24][C:23](=O)[CH2:22]1)#[N:19]>O1CCCC1>[C:18]([CH2:20][C:21]1([C:26]#[N:27])[CH2:24][C:23](=[CH:9][C:7]#[N:8])[CH2:22]1)#[N:19]

Participants

5

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 668242591-(Cyanomethyl)-3-oxocyclobutanecarbonitrile

Product 1

HCID 866635061-(Cyanomethyl)-3-(cyanomethylene)cyclobutanecarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1.0 M of potassium tert-butoxide in tetrahydrofuran (2.15 mL) at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (0.364 mL, 0.00225 mol) in tetrahydrofuran (4 mL, 0.04 mol). The reaction was warmed to rt and then cooled to 0° C. again. To the reaction mixture was added a solution of 1-(cyanomethyl)-3-oxocyclobutanecarbonitrile (0.274 g, 0.00204 mol) in tetrahydrofuran (2 mL, 0.02 mol). The reaction was allowed to warm up to rt and stirred at rt overnight. After quenching with water, the mixture was extracted with ether. The combined organic layers were washed with water and brine, then dried and evaporated to dryness. The crude mixture was used directly in next step.

Workup

  1. temperaturecooled to 0° C. again
  2. temperatureto warm up to rt
  3. customAfter quenching with water
  4. extractionthe mixture was extracted with ether
  5. washThe combined organic layers were washed with water and brine
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-1ecc81b8e0754cb59ca81bb28a66fadd
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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