Hydrochloric Acid → HCID 59424843, Verbindung

HRID 501502

Reaktionsgleichung

Reaktionsgleichung von HRID 501502
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[F:11])=[O:3].C([Si](C(C)C)(C(C)C)[S:16][C:17]1[CH:18]=[C:19]([C:23]2([C:29]([NH2:31])=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)([O-])C.[K+].Cl>C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:16][C:17]2[CH:18]=[C:19]([C:23]3([C:29]([NH2:31])=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:20]=[CH:21][CH:22]=2)=[CH:6][C:5]=1[F:11])(=[O:3])[CH3:1]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 677702,4-DifluoroacetophenoneHCID 2724141Tetrabutylammonium FluorideHCID 23665647Potassium tert-butoxideHCID 566014104-(3-(triisopropylsilylthio)phenyl)tetrahydro-2H-pyran-4-carboxamide

Produkt 1

HCID 59424843HCID 59424843, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2,4-Difluoroacetophenone (0.40 g, 2.54 mmols), 4-{3-[(triisopropylsilyl)thio]phenyl}-tetra-hydro-2H-pyran-4-carboxamide (1.0 g, 2.54 mmols), tetrabutylammonium fluoride (0.66 g, 2.54 mmols), and potassium tert-butoxide (1.0 M in THF, 2.54 ml, 2.54 mmols) were added to anhydrous toluene (10 ml). The mixture was warmed to 90 degrees Celcius and stirred for 4 hours. After cooling to room temperature, ethyl acetate was added (100 ml) along with 1.0 N HCl (6 ml). The mixture was then stirred for 30 minutes and a beige precipate was collected by suction filtration. The crude product was purified further on silica gel eluting with a 70:30 mixture of methylene chloride and acetone. The appropriate fractions were concentrated to a light brown solid, (0.61 g, 64%).

Aufarbeitung

  1. temperatureThe mixture was warmed to 90 degrees Celcius
  2. stirringThe mixture was then stirred for 30 minutes
  3. filtrationa beige precipate was collected by suction filtration
  4. customThe crude product was purified further on silica gel eluting with a 70:30 mixture of methylene chloride and acetone
  5. concentrationThe appropriate fractions were concentrated to a light brown solid, (0.61 g, 64%)

Quellen und Nachweise

ORD-Eintrag
ord-5657c0da012f435683a36db2faaed799
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772269B2

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