N-Methoxy-N-methylbenzamide → 1-Phenyl-2-(4-(methylthio)phenyl)ethanone

HRID 322042

Reaction equation

CON(C)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:13][S:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][Mg]Cl)=[CH:17][CH:16]=1>C1COCC1>[C:5]1([C:4](=[O:11])[CH2:19][C:18]2[CH:22]=[CH:23][C:15]([S:14][CH3:13])=[CH:16][CH:17]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution ot N-methoxy-N-methylbenzamide (409 mg, 2.27 mmol) in THF (22mL) was added a THF solution (5.0 mL, 0.5 M) of 4-(methylthio)benzylmagnesium chloride (J.Org. Chem. 42, 1914, 1977). The mixture was stirred at 0° C. for 3 h, NH4OAc was added and the mixture was extracted with EtOAc. The EtOAc extracts were washed with brine, dried over MgSO4, filtered and concentrated to an oil. Chromatography of the oil on silica gel (eluted with 2.5% EtOAc/toluene) gave 501 mg of the title compound.

Workup

extractionthe mixture was extracted with EtOAc
washThe EtOAc extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to an oil

Sources & evidence

ORD record: ord-8a94cb206bb9497bb4c780716b1fd9b0
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211210B1

Linked notes

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