Hydrochloric Acid → [5-(4-Fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol

HRID 554290Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:11]([CH3:22])=[C:10]([C:23](OCC)=[O:24])[CH:9]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:11]([CH3:22])=[C:10]([CH2:23][OH:24])[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Ethyl 5-(4-fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (2.70 g) was dissolved in tetrahydrofuran (30 mL), and the mixture was cooled to −78° C. A 1.5 mol/L toluene solution (13.1 mL) of diisobutylaluminum hydride was added dropwise, and the mixture was further stirred at −78° C. for 2 hr. 1 mol/L Hydrochloric acid (15 mL) was added to the reaction mixture, and the mixture was diluted with ethyl acetate. The insoluble material was filtered through celite, and the filtrate was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:3) to give the title compound as an oil (yield 1.09 g, 45%).

Workup

filtrationThe insoluble material was filtered through celite
extractionthe filtrate was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:3)

Sources & evidence

ORD record: ord-236fd988ed314d82b36e24eade426fe2
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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