2-Pyrrolidone → HCID 19811007, compound

HRID 373709Notes

Reaction equation

HRID 373709 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C([Li])CCC.[C:12]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>O1CCCC1.CCCCCC>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])(=[O:24])=[O:23])=[CH:18][CH:17]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 120252-PyrrolidoneHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 19811007HCID 19811007, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

1.65 g of 2-pyrrolidinone in solution in 75 cm3 of tetrahydrofuran is cooled to -5° C., and 12.1 cm3 of a 1.6M solution of n-butyllithium in hexane is added, maintaining the temperature between -5° C. and 0° C. Agitation is carried out for 25 minutes at -5° C.; the mixture is cooled to -20° C. and 4.5 g of 4-tert-butyl-phenylsulphonyl chloride is added [Recueil Trav. Chim. Pays-Bas, 53, 1101 (1934)]. After allowing to return to ambient temperature, the tetrahydrofuran is evaporated off under reduced pressure, the residue is taken up with water, filtered and crystallized from ethanol. 2.75 g of expected product is obtained.

Workup

  1. temperaturemaintaining the temperature between -5° C. and 0° C
  2. customto return to ambient temperature
  3. customthe tetrahydrofuran is evaporated off under reduced pressure
  4. filtrationfiltered
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-82b20aec96444e268969e5d08fc974e3
Source dataset
uspto-grants-1992_11
Patent number
US05164514

Reaction notes

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