Water → (NZ)-N-[1-(4-butoxyphenyl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 1629797Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH3:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:15][C:16]([S:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].O>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](=[N:21]\[S:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20])/[CH3:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 1-(4-butoxyphenyl)ethanone (3 g, 15.60 mmol) and 2-methylpropane-2-sulfinamide (2.84 g, 23.41 mmol) in THF (50 mL) was added tetraethoxytitanium (8.90 g, 39.0 mmol). The reaction was heated to 70° C. for 3 d. Cold water was added and the reaction was stirred vigorously for 20 min. The mixture was filtered through Celite® and the filtrated was diluted with EtOAc. The organic solution was washed with H2O, brine, dried over MgSO4, filtered and concentrated. The crude product was by silica gel chromatography (220 g silica gel, eluted with EtOAc in hexanes) to yield the desired product (4 g, 87%) as a yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.88 (d, J=8.80 Hz, 2H), 6.91 (d, J=8.80 Hz, 2H), 4.02 (t, J=6.46 Hz, 2H), 2.73 (s, 3H), 1.75-1.83 (m, 2H), 1.46-1.56 (m, 2H), 1.32 (s, 9H), 0.99 (t, J=7.43 Hz, 3H).

Workup

filtrationThe mixture was filtered through Celite®
additionthe filtrated was diluted with EtOAc
washThe organic solution was washed with H2O, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
washThe crude product was by silica gel chromatography (220 g silica gel, eluted with EtOAc in hexanes)

Sources & evidence

ORD record: ord-a983141af41d4b7fa0dbce83c168b1d6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791091B2

Reaction notes

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