Triphenylphosphine → HCID 58474520, compound

HRID 1400853Notes

Reaction equation

HRID 1400853 reaction equation
[Br:1][C:2]1C=CNN=1.O[CH2:8][CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO[C:38](/[N:40]=[N:41]/[C:42](OCC)=O)=O>C1COCC1>[Br:1][C:2]1[CH:42]=[N:41][N:40]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:38]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 5462977Diethyl azodicarboxylateHCID 178419412HCID 178419412, compound

Product 1

HCID 58474520HCID 58474520, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromopyrazole (5 g, 34 mmol), 1-(2-hydroxyethyl)pyrrolidin-2-one (5.75 g, 51 mmol), PPh3 (13.38 g, 51 mmol) in THF (100 mL) was added DEAD (8.89 g, 51 mmol) and the reaction mixture was stirred at RT overnight. The mixture was concentrated, co-evaporated with Et2O then dissolved in Et2O and cooled in a fridge for 3 hrs whereupon Ph3P═O precipitated out. The mixture was then filtered and concentrated to afford title compound 162 (8.78 g, 100% yield) which was used in the next step with no additional purification. MS (m/z) 259.12/261.12 (M+H).

Workup

  1. concentrationThe mixture was concentrated, co-evaporated with Et2O
  2. dissolutionthen dissolved in Et2O
  3. temperaturecooled in a fridge for 3 hrs whereupon Ph3P═O
  4. customprecipitated out
  5. filtrationThe mixture was then filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c3f7f7b5bd84abea972406ffdca4381
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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