Diethyl (cyanomethyl)phosphonate → [3-(Benzyloxy)cyclobutylidene]acetonitrile

HRID 1966172Notes

Reaction equation

HRID 1966172 reaction equation
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[CH2:18]([O:25][CH:26]1[CH2:29][C:28](=O)[CH2:27]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[CH2:18]([O:25][CH:26]1[CH2:29][C:28](=[CH:9][C:7]#[N:8])[CH2:27]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 149327873-(Benzyloxy)cyclobutan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 66824115[3-(Benzyloxy)cyclobutylidene]acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of 1.0000 M of potassium tert-butoxide in tetrahydrofuran (0.68 mL) and THF (5 mL) was added, at 0° C., diethyl cyanomethylphosphonate (0.11 mL, 0.00068 mol) dropwise. The reaction was warmed to rt and 30 min later cooled to 0° C. again. To the reaction mixture was added a solution of 3-(benzyloxy)cyclobutanone (0.1 g, 0.0006 mol) in THF (5 mL). The reaction was stirred over night, allowing warmed up to rt. The reaction was quenched with saturated aq. NH4Cl solution, extracted with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated to dryness. The crude product was used directly in next step without further purification.

Workup

  1. additionwas added, at 0° C.
  2. temperaturelater cooled to 0° C. again
  3. temperatureallowing warmed up to rt
  4. customThe reaction was quenched with saturated aq. NH4Cl solution
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to dryness
  9. customThe crude product was used directly in next step without further purification

Sources & evidence

ORD record
ord-ffac4566bee046229c6b441f76ebc9a0
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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