Formic Acid → 5-Hydroxymethyl-6-phenyl-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 909310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909310
[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2OS(C(F)(F)F)(=O)=O)=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:29])=[CH:6][C:7]([CH3:28])([CH3:27])[NH:8]2.C(N(CC)CC)C.C(O)=O>CN(C)C=O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:29])=[CH:6][C:7]([CH3:28])([CH3:27])[NH:8]2

Komponenten

7

Edukt 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 584854825-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Produkt 1

HCID 580267805-Hydroxymethyl-6-phenyl-2,2,4-trimethyl-1,2-dihydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

5-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 6-1, 136 mg, 0.318 mmol) was dissolved in anhydrous N,N-dimethylformamide (1.5 mL), then the solvent was bubbled with argon for 2 minutes, and then tetrakis(triphenylphosphine)palladium(0) (35.6 mg, 0.0308 mmol), triethylamine (221 μL, 1.59 mmol) and formic acid (60 μL, 1.6 mmol) were added thereto. After the reaction mixture was stirred at 60° C. for 10 hours, it was diluted with ethyl acetate (50 mL). The whole was washed with saturated NaHCO3 solution (30 mL) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (93.0 mg) as a yellow oil. (quantative)

Aufarbeitung

  1. customthe solvent was bubbled with argon for 2 minutes
  2. washThe whole was washed with saturated NaHCO3 solution (30 mL) and saturated brine (30 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a19949493bd94595a5dee00b7c6ff708
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017775B2

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