P-Chloroacetophenone → HCID 86722006, Verbindung

HRID 1398042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398042
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([C:8](Cl)=[O:9])[CH2:5][CH2:4][O:3]1.CCOCC.[Mg+2].[Br-].[Br-].[CH3:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[O:22].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23](/[C:21](/[OH:22])=[CH:20]/[C:8]([CH:6]2[CH2:5][CH2:4][O:3][C:2]([CH3:11])([CH3:1])[CH2:7]2)=[O:9])=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 7467P-ChloroacetophenoneHCID 81531DiisopropylethylamineHCID 9903262Magnesium bromide diethyl etherateHCID 122964132,2-dimethyltetrahydro-2H-pyran-4-carbonyl chloride

Produkt 1

HCID 86722006HCID 86722006, VerbindungAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 2,2-dimethyltetrahydro-2H-pyran-4-carbonyl chloride (0.55 g, 3.14 mmol), magnesium bromide diethyl etherate (1.35 g, 5.23 mmol), and 4-chloroacetophenone (0.34 mL, 2.62 mmol) in 12 mL of DCM at RT was added dropwise DIEA (1.45 mL, 7.85 mmol). The mixture was stirred overnight and then diluted with 50 mL of DCM and washed with 1N HCl (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, concentrated, and the crude product was purified by silica gel chromatography (Thomson Scientific 25-g cartridge, 2-20% EtOAc/heptane in 10 column volumes) to give 0.45 g (58%) of the title compound as a light orange solid. The NMR of this compound shows that it exists in the enone form in CDCl3.

Aufarbeitung

  1. washwashed with 1N HCl (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe crude product was purified by silica gel chromatography (Thomson Scientific 25-g cartridge, 2-20% EtOAc/heptane in 10 column volumes)

Quellen und Nachweise

ORD-Eintrag
ord-2bc7bdd3851441c28a03dbcce7d8ca87
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901314B2

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