Sodium hydride → HCID 66824398, compound

HRID 1692908Notes

Reaction equation

HRID 1692908 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[O:14]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:22][C:21](=O)[CH2:20]2)=[N:15]1>O1CCCC1>[O:14]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:22][C:21](=[CH:5][C:3]#[N:4])[CH2:20]2)=[N:15]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 57868840HCID 57868840, compound

Product 1

HCID 66824398HCID 66824398, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 75 mg, 1.88 mmol) was added at once to a solution of diethyl cyanomethylphosphonate (0.33 mL, 2.1 mmol) in tetrahydrofuran (8 mL). After stirring for 5 minutes, a solution of 3-isoxazol-3-ylcyclobutanone (258 mg, 1.88 mmol) in tetrahydrofuran (20 mL) was added. After 2 hours reaction time, the reaction mixture was partitioned between ethyl acetate and brine and the layers separated. The aqueous layer was extracted with two further portions of ethyl acetate and the combined extracts were dried over sodium sulfate, decanted and concentrated. The residue was then azeotroped with toluene and the product was used without further purification in Step 9.

Workup

  1. customAfter 2 hours reaction time
  2. customthe reaction mixture was partitioned between ethyl acetate and brine
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with two further portions of ethyl acetate
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. customdecanted
  7. concentrationconcentrated
  8. customThe residue was then azeotroped with toluene
  9. customthe product was used without further purification in Step 9

Sources & evidence

ORD record
ord-d8ea3782dded42b48a30fc92b36ee0fd
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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