(Triphenylphosphoranylidene)acetonitrile → HCID 69587016, compound

HRID 1612412Notes

Reaction equation

HRID 1612412 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1.C1(P(=[CH:33][C:34]#[N:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:33][C:34]#[N:35])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 19363032Methyl 2-(4-formylphenyl)acetate

Product 1

HCID 69587016HCID 69587016, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirring solution of 30 in benzene (0.4 M) at room temperature under nitrogen was added (triphenylphosphoranylidene)acetonitrile (1.1 eq). The reaction was refluxed overnight. The benzene was removed under reduced pressure. The resulting oil was dissolved in ethyl acetate and washed with 1N hydrochloric acid (1×), saturated sodium bicarbonate (1×) and brine (1×) then dried over sodium sulfate, filtered, concentrated in vacuo and purified by flash chromatography using the ISCO (0-15% gradient methanol/dichloromethane). (98%) 1H NMR (400 MHz, CDCl3) δ 7.31-7.44 (m, 5H), 5.87 (d, 1H), 3.71 (s, 3H), 3.66 (s, 2H).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customThe benzene was removed under reduced pressure
  3. dissolutionThe resulting oil was dissolved in ethyl acetate
  4. washwashed with 1N hydrochloric acid (1×), saturated sodium bicarbonate (1×) and brine (1×)
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-27beab583b9b4c149656a3214a4dcab4
Source dataset
uspto-grants-2006_01
Patent number
US06992193B2

Reaction notes

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