Benzenesulfonyl chloride → HCID 21611515, compound

HRID 476645Notes

Reaction equation

HRID 476645 reaction equation
C([Li])CCC.[CH2:6]([O:12][CH:13]1[NH:17][C:16](=[O:18])[CH:15]=[CH:14]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCCCCC.O1CCCC1>[C:19]1([S:25]([N:17]2[CH:13]([O:12][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:14]=[CH:15][C:16]2=[O:18])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 19838059HCID 19838059, compoundHCID 178418339Butyllithium

Product 1

HCID 21611515HCID 21611515, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-30 °C

Procedure

39.37 cm3 of a 1.4M solution of n-butyllithium in n-hexane is added to a solution of 10.1 g of 1,5-dihydro-5-n-hexyloxy-2H-pyrrol-2-one obtained at stage A in 170 cm3 of tetrahydrofuran cooled to -30° C. The temperature is maintained at -30° C. while agitating for 15 minutes, then is reduced to -35° C. and a solution of 9.73 g of benzenesulphonyl chloride in 70 cm3 of tetrahydrofuran is added, while maintaining the temperature at between -35° C. and -53° C. 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, 1-2). 5.68 g of the expected product is obtained.

Workup

  1. temperatureThe temperature is maintained at -30° C.
  2. customis reduced to -35° C.
  3. temperaturewhile maintaining the temperature at between -35° C. and -53° C
  4. customthe solvent is evaporated under reduced pressure
  5. customthe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1-2)

Sources & evidence

ORD record
ord-942ee61af7f54735aa13df1bf9286ced
Source dataset
uspto-grants-1989_12
Patent number
US04885307

Reaction notes

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