Sodium hydride → HCID 66824398, compound

HRID 1966140Notes

Reaction equation

HRID 1966140 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-904282414d82458a85ad193fb3d09fda
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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