Acetone → HCID 20446887, compound

HRID 1463078Notes

Reaction equation

HRID 1463078 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([N:7]2[CH2:11][CH:10]=[C:9]([O:12][Si](C(C)(C)C)(C)C)[NH:8]2)=[CH:3][CH:2]=1.C([Li])CCC.[CH3:26][C:27]([CH3:29])=[O:28]>O1CCCC1.CCCCCC>[OH:28][C:27]([CH:10]1[CH2:11][N:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:20])=[CH:6][CH:5]=2)[NH:8][C:9]1=[O:12])([CH3:29])[CH3:26]

Participants

6

Reactant 3

HCID 180AcetoneHCID 70509673HCID 70509673, compoundHCID 178418339Butyllithium

Product 1

HCID 20446887HCID 20446887, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1-p-tolyl-3-(t-butyldimethylsiloxy)-pyrazoline (218 g, 0.75 mole) in 750 ml anhydrous tetrahydrofuran was added dropwise over a 30 minute period to a solution of n-butyllithium (51.5 g, 0.80 mole) in 350 ml n-hexane and 3.0 l anhydrous tetrahydrofuran stirred under nitrogen and cooled to -78° C. in a dry ice-acetone bath. The mixture was stirred for another 30 minutes then treated with one portion of acetone (58. g, 1.0 mole), and stirred at -78° C. for an additional 30 minutes. After removal of the dry ice-acetone bath, one portion of 250 ml 5% aqueous hydrochloric acid was added and the mixture was stirred an additional 25 minutes. The mixture was extracted with 1.0 l of ether and then with a (1:1) mixture of ether and ethyl acetate. The combined extracts were dried over magnesium sulfate. After removal of solvent, the residue was digested in a hot (3:2) mixture of ether and n-hexane. Upon cooling to 0° C. and filtering, 111 g of 4-(1-hydroxy-1-methylethyl)-1-p-tolyl-3-pyrazolidinone was obtained. Analysis was confirmed by infrared and NMR spectra.

Workup

  1. stirringThe mixture was stirred for another 30 minutes
  2. stirringstirred at -78° C. for an additional 30 minutes
  3. customAfter removal of the dry ice-acetone bath, one portion of 250 ml 5% aqueous hydrochloric acid
  4. additionwas added
  5. stirringthe mixture was stirred an additional 25 minutes
  6. extractionThe mixture was extracted with 1.0 l of ether
  7. additionwith a (1:1) mixture of ether and ethyl acetate
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. customAfter removal of solvent
  10. additionthe residue was digested in a hot (3:2) mixture of ether and n-hexane
  11. temperatureUpon cooling to 0° C.
  12. filtrationfiltering

Sources & evidence

ORD record
ord-ba504f124163441cb5b5bb4e9eb20e7a
Source dataset
uspto-grants-1984_07
Patent number
US04463081

Reaction notes

Loading…