Methanesulfonic Acid → Methyl(4-fluoro-6-methoxy-1-benzothiophen-3-yl)acetate

HRID 591561Notes

Reaction equation

S(O)(C)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([S:15][CH2:16][C:17](=O)[CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1>O>[CH3:22][O:21][C:19](=[O:20])[CH2:18][C:17]1[C:8]2[C:7]([F:6])=[CH:12][C:11]([O:13][CH3:14])=[CH:10][C:9]=2[S:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

MsOH (13.68 mL) was added dropwise to methyl 4-((3-fluoro-5-methoxyphenyl)sulfanyl)-3-oxobutanoate (2.87 g) at 0° C. The mixture was stirred at 0° C. for 30 min. The mixture was poured into iced water and extracted with EtOAc. The organic layer was separated, washed successively with water, saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (900 mg).

Workup

extractionextracted with EtOAc
customThe organic layer was separated
washwashed successively with water, saturated aqueous NaHCO3 and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record: ord-64e057bd6688444b9a8cb568ede9e004
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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