Diethyl (cyanomethyl)phosphonate → HCID 66824449, compound

HRID 1692926Notes

Reaction equation

HRID 1692926 reaction equation
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[F:18][CH2:19][C:20]1([C:25]#[N:26])[CH2:23][C:22](=O)[CH2:21]1>O1CCCC1>[C:7]([CH:9]=[C:22]1[CH2:23][C:20]([CH2:19][F:18])([C:25]#[N:26])[CH2:21]1)#[N:8]

Participants

5

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 66824419HCID 66824419, compound

Product 1

HCID 66824449HCID 66824449, compound

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-(fluoromethyl)-3-oxocyclobutanecarbonitrile (0.260 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 then brine, 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
  6. dry with materialbrine, dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-94353a1e595445cc99ad29277304e379
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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