1-(Triphenylphosphoranylidene)acetone → [1-(3-Oxobut-1-en-1-yl)cyclopropyl]acetonitrile

HRID 1683980Notes

Reaction equation

HRID 1683980 reaction equation
O=[CH:2][CH2:3][C:4]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5]1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:17][C:18](=[O:20])C)C=CC=CC=1>C1COCC1>[O:20]=[C:18]([CH3:17])[CH:2]=[CH:3][C:4]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 19041707[1-(2-Oxoethyl)cyclopropyl]acetonitrile

Product 1

HCID 53970073[1-(3-Oxobut-1-en-1-yl)cyclopropyl]acetonitrileYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the aldehyde from Example 1, Step 2 (8.12 g, 75 mmol) and 1-triphenylphosphoranylidene-2-propanone (26.4 g, 83 mmol) in 250 mL THF was heated to reflux overnight. The reaction mixture was partitioned between 1N HCl and ethyl acetate, and the organic layer was washed with brine, dried over MgSO4 and evaporated. Et2O was added to the residue, the phosphine oxide was filtered off and the solvent removed in vacuo. Purification through a plug of silica gel provided 10.3 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. additionEt2O was added to the residue
  8. filtrationthe phosphine oxide was filtered off
  9. customthe solvent removed in vacuo
  10. customPurification through a plug of silica gel

Sources & evidence

ORD record
ord-2d4d291cacaa40c3805014381948b90c
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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