Hydrochloric Acid → HCID 66925005, compound

HRID 554287Notes

Reaction equation

HRID 554287 reaction equation
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([C:26](OCC)=[O:27])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]([F:25])([F:23])[F:24])=[CH:19][CH:20]=3)(=[O:13])=[O:14])[CH:10]=[C:9]([CH2:26][OH:27])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 66924637HCID 66924637, compound

Product 1

HCID 66925005HCID 66925005, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A solution (30 mL) of ethyl 5-phenyl-1-{[4-(trifluoromethoxy)phenyl]sulfonyl}-1H-pyrrole-3-carboxylate (1.33 g) in tetrahydrofuran was cooled to −78° C., a 1.5 mol/L solution (8.0 mL) of diisobutylaluminum hydride in toluene was added dropwise, and the mixture was further stirred at −78° C. for 3 hr. 1 mol/L hydrochloric acid (20 mL) was added to the reaction mixture, and the mixture was diluted with ethyl acetate. 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=3:2) to give the title compound as an oil (yield 0.71 g, 59%).

Workup

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

Sources & evidence

ORD record
ord-423470958e01497a92d5c0cf8d2fb50d
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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