Diethyl (cyanomethyl)phosphonate → HCID 86634346, compound

HRID 1966162Notes

Reaction equation

HRID 1966162 reaction equation
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].O=[C:19]1[CH2:22][C:21]([CH2:26][C:27]#[N:28])([CH2:23][C:24]#[N:25])[CH2:20]1>O1CCCC1>[C:21]1([CH2:26][C:27]#[N:28])([CH2:23][C:24]#[N:25])[CH2:22][C:19](=[CH:9][C:7]#[N:8])[CH2:20]1

Participants

5

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 66824283HCID 66824283, compound

Product 1

HCID 86634346HCID 86634346, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.0 M of potassium tert-butoxide in tetrahydrofuran (5.1 mL) was added dropwise at 0° C. diethyl cyanomethylphosphonate (0.82 mL, 0.0051 mol). The reaction was warmed to rt and 30 min later cooled to 0° C. again. To the reaction mixture was added a solution of 2,2′-(3-oxocyclobutane-1,1-diyl)diacetonitrile (0.5 g, 0.003 mol) in THF (5 mL). The reaction was allowed to warm up to rt gradually and stirred at rt for 2 h. The reaction was quenched with saturated aq. NH4Cl, then extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to give a brown oily crude product, which was used directly in the next step.

Workup

  1. temperaturelater cooled to 0° C. again
  2. temperatureto warm up to rt gradually
  3. customThe reaction was quenched with saturated aq. NH4Cl
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4f89b391695543eb8f35cab784511bfc
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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