Ethyl Acetate → 2-Methyl-N-{1-[4-(propylsulphonyl)phenyl]prop-2-en-1-yl}propane-2-sulphinamide

HRID 1698511Notes

Reaction equation

[CH:1]([Mg]Br)=[CH2:2].[CH3:5][C:6]([S:9](/[N:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])=[CH:15][CH:14]=1)=[O:10])([CH3:8])[CH3:7].C(OCC)(=O)C>C1COCC1.CCCCCC>[CH3:8][C:6]([S:9]([NH:11][CH:12]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])=[CH:17][CH:18]=1)[CH:1]=[CH2:2])=[O:10])([CH3:5])[CH3:7]

Participants

Conditions

Temperature: -78 °C

Procedure

Vinylmagnesium bromide (3.3 mL of a 1.0 M solution in THF, 3.3 mmol) was added dropwise to a solution of 2-methyl-N-{(1E)-[4-(propylsulphonyl)phenyl]methylene}-propane-2-sulphinamide (1.0 g, 3.17 mmol, prepared as described in Example 50a in THF (15 mL) at −78° C. The mixture was stirred at −78° C. for 6 h and then allowed to warm to room temperature overnight. The reaction mixture was quenched by addition of saturated NH4Cl(aq) and the product extracted into ethyl acetate (×2). The combined organic extracts were dried (MgSO4) and concentrated. The product was purified by gradient chromatography on silica eluting with 30 to 80% ethyl acetate in hexane giving the title compound as a yellow solid (485 mg, 45% yield). m/z (ES+) 366 (M+Na), 344 (M+H).

Workup

customprepared
temperatureto warm to room temperature overnight
customThe reaction mixture was quenched by addition of saturated NH4Cl(aq)
extractionthe product extracted into ethyl acetate (×2)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-2e124de7cab8495c95de7fdbe46f2cab
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163956B2

Reaction notes

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