Benzenesulfonyl chloride → HCID 19838065, compound

HRID 476637Notes

Reaction equation

HRID 476637 reaction equation
C([Li])CCC.[CH2:6]([O:8][CH:9]1[NH:13][C:12](=[O:14])[CH:11]=[CH:10]1)[CH3:7].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCCC.O1CCCC1>[C:15]1([S:21]([N:13]2[CH:9]([O:8][CH2:6][CH3:7])[CH:10]=[CH:11][C:12]2=[O:14])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 133284325-Ethoxy-1,5-dihydro-2H-pyrrol-2-oneHCID 178418339Butyllithium

Product 1

HCID 19838065HCID 19838065, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-35 °C

Procedure

7.37 cm3 of a 1.6M solution of n-butyllithium in n-hexane is added to a solution of 1.5 g of 1,5-dihydro-5-ethoxy-2H-pyrrol-2-one in 40 cm3 of tetrahydrofuran cooled to -35° C., operating at -35°/-30° C. The mixture is agitated for 20 minutes, then cooled to -40° C., and while maintaining the temperature between -38° C. and -40° C., a solution is added of 2.08 g of benzene sulphonyl chloride in 10 cm3 of tetrahydrofuran. The temperature is allowed to return to the ambient, the solvent is evaporated under reduced pressure, and the residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1). 1.15 g of the expected product is obtained. m.p. 117°-119° C., crystallized from ethyl ether.

Workup

  1. customoperating at -35°
  2. custom-30° C
  3. temperaturecooled to -40° C.
  4. temperaturewhile maintaining the temperature between -38° C. and -40° C.
  5. customthe solvent is evaporated under reduced pressure
  6. customthe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1)

Sources & evidence

ORD record
ord-f5aad58be9c24afe8e9fc2cca345f486
Source dataset
uspto-grants-1989_12
Patent number
US04885307

Reaction notes

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