Benzenesulfonyl chloride → HCID 19838070, compound

HRID 476642Notes

Reaction equation

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

Participants

Conditions

Temperature: -40 °C

Procedure

13.2 cm3 of a 1.6M solution of n-butyllithium in hexane is added to a solution cooled to -45° C. of 3.3 g of 1,5-dihydro-5-isobutyloxy-2H-pyrrol-2-one obtained at stage A, in 80 cm3 of tetrahydrofuran. The mixture is agitated for 30 minutes at -45° C./-40° C., then a solution of 3.74 g of benzenesulphonyl chloride in 12 cm3 of tetrahydrofuran is added. The temperature is allowed to return to the ambient over 2 hours. After evaporating to dryness, the residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1), and 1.7 g of the expected product is obtained. m.p. 82°-83° C., crystallized from isopropanol.

Workup

waitto return to the ambient over 2 hours
customAfter evaporating to dryness
customthe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1)

Sources & evidence

ORD record: ord-53da33d707444b7f8fd96c6abc2d9f9e
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04885307

Reaction notes

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