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

HRID 741679

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 of N-methoxy-N-methylbenzamide (409 mg, 2.27 mmol) in THF (22mL) was added a THF solution (5.0 mL, 0.5M) 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-5f5e8e8e3d2643388350f86374a0bebe
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05552422

Linked notes

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