Ethenesulfonyl chloride, 2-phenyl- → HCID 3087418, compound

HRID 1193504Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[NH:3]1.C([Li])CCC.[CH:15]([S:23](Cl)(=[O:25])=[O:24])=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[CH:15]([S:23]([N:3]1[CH:4]([O:7][CH2:8][CH3:9])[CH2:5][CH2:6][C:2]1=[O:1])(=[O:25])=[O:24])=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: -5 °C

Procedure

2.6 g of 2-oxo-5-ethoxy pyrrolidine is dissolved in 80 cm3 of anhydrous tetrahydrofuran, then cooled to -5° C., and 12.6 cm3 of butyllithium is added. After 20 minutes under agitation, there is added slowly at the same temperature, 4.05 g of styrene-sulphonyl chloride (CA 47, 3262c (1953)) in 10 cm3 of tetrahydrofuran. After allowing this to return to ambient temperature, after 4 hours, it is concentrated to dryness and the residue is chromatographed on silica. 1.3 g of the expected product is obtained, which is crystallized from a mixture of ethyl ether and hexane. m.p.=61°-63° C.

Workup

concentrationit is concentrated to dryness
customthe residue is chromatographed on silica

Sources & evidence

ORD record: ord-29368e2b03694131b0ca3aa0ddf59d92
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04810722

Reaction notes

Loading…